GOEKE, Judge: Respondent determined deficiencies in petitioner's 2007 and 2008 Federal income tax of $15,257 ¹ and $54,862, respectively. Respondent *246 also determined section 6662(a)² accuracy-related penalties for 2007 and 2008 of $3,051 and $10,972, respectively. Finally, respondent determined a section 6651(a)(1) failure to file addition to tax for 2008 of $8,555. After concessions, ³ the issues for decision are:

(1) whether petitioner is entitled to deductions of $39,402 and $50,491 for disputed expenses reported on Schedule C, Profit or Loss From Business, for 2007 and 2008, respectively. We hold that he is not;

(2) whether petitioner is entitled to deductions of $94,603 and $83,874 for disputed mortgage interest expenses reported on Schedule E, Supplemental Income and Loss, for 2007 and 2008, respectively. We hold that he is not;

(3) whether petitioner is entitled to a deduction of $14,419 for disputed Schedule E real property tax expenses for 2008. We hold that he is not;

(4) whether petitioner failed to report discharge of indebtedness 2012 Tax Ct. Memo LEXIS 241">*242 income of $105,599 for 2008. We hold that he did not;

*247 (5) whether petitioner is liable for section 6662(a) accuracy-related penalties for 2007 and 2008. We hold that he is; and

(6) whether petitioner is liable for the section 6651(a)(1) failure to file addition to tax for 2008. We hold that he is.

At the time the petition was filed, petitioner resided in Maryland. In both 2007 and 2008 petitioner lived in Boston, Massachusetts, and worked at a hospital as a clinical systems developer.

Petitioner began investing in rental real estate in and around Chicago, Illinois, 2012 Tax Ct. Memo LEXIS 241">*243 during 2002. He also started a real estate brokerage, ABA National Realty, LLC, in 2005, of which he was the sole owner. Petitioner was a real estate broker and participated in rental real estate activities in Chicago during both 2007 and 2008. The parties stipulated that petitioner's rental real estate activities in 2007 and 2008 were passive activities in which he did not materially participate.

Petitioner claimed mortgage interest expense deductions for various rental properties on Schedule E. The following mortgage interest expense deductions are in dispute for 2007 and 2008:

Petitioner is not the person named as the borrower for any of the mortgages on these properties. Christopher Hart is the person named on the mortgages for 21 E. Huron St. #2206 and 2428 Avalon Ct. Mark Faruzzi is the person named on two mortgages for 21 E. Huron St. #2901, and Elsa Abarca is the person named on the mortgage for 2012 Tax Ct. Memo LEXIS 241">*244 652 Nantucket Way. The borrower information was not provided for the mortgages for 704 Blue Ridge and 243 N. Garfield. Although he was not the borrower for any of these mortgages, petitioner made certain mortgage payments for 21 E. Huron St. #2206, 21 E. Huron St. #2901, and 2428 Avalon Ct., as discussed infra.

Petitioner entered into separate partnership agreements with Mr. Hart and Mr. Faruzzi for operation of the rental properties at 21 E. Huron St. #2206, 21 E. *249 Huron St. #2901, and 2428 Avalon Ct. ⁴ The partnership agreements appear to be form agreements intended for use in the United Kingdom. The partnerships were formed because petitioner was attempting to buy additional properties but had an insufficient amount of credit available to do so.

Each partnership agreement provided that petitioner would contribute the initial partnership capital and that the other partner would use his credit to obtain a loan in order to purchase a rental property identified in the partnership agreement. It was unclear whether titles to the purchased properties were ever contributed to the corresponding partnerships, but it was 2012 Tax Ct. Memo LEXIS 241">*245 established that petitioner did not hold title to any of the partnership properties. Each partnership agreement provided that petitioner would pay a percentage of the expenses associated with the rental property as well as manage the property. Finally, each partnership agreement also provided that both partners would share the profits or losses for each partnership year in proportion to their partnership interests. No evidence that partnership formalities were followed was produced, and petitioner did not properly account *250 for their existence on his 2007 and 2008 tax returns. Rather, petitioner filed his tax returns as if he owned each property directly. ⁵

Petitioner did not hold title to the 652 Nantucket Way, 704 Blue Ridge, and 243 N. Garfield properties previously listed. In addition, petitioner did not hold title to a property at 3010 Ilene. However, on his 2008 tax return petitioner deducted $14,419 in real property tax paid on these properties. Whether petitioner actually paid the real property tax is discussed infra.

Petitioner claimed deductions for car and truck use, rent, travel, and meals and entertainment on Schedules C for both 2007 and 2008. While petitioner substantiated (and respondent accordingly allowed) portions of the car and truck expense deductions for both years, respondent disallowed the following deductions: (1) car and truck expenses of $9,095 and $8,677 for 2007 and 2008, respectively; (2) rent expenses of $17,190 and $19,797 for 2007 and 2008, respectively; (3) meals and entertainment expenses of $1,442 and $2,721 for 2007 and 2008, respectively; and (4) travel expenses of $11,675 and $19,296 for 2007 *251 and 2008, respectively, resulting from petitioner's travel between Chicago and Boston. Other information regarding the claimed expenses is discussed infra.

On June 30, 2008, petitioner sold a property at 201 N. Westshore Drive #707, Chicago, Illinois. At the time of sale, J.P. Morgan Chase (J.P. Morgan) held two mortgages on the property with balances due totaling $471,787 for which petitioner was liable. ⁶ With the proceeds of the sale, petitioner was able to pay J.P. Morgan only $105,599 less than the balances due on its mortgages. 2012 Tax Ct. Memo LEXIS 241">*247 ⁷ The unpaid amount was "charged off" at some unestablished point before July 12, 2010, by an unestablished entity.

On September 12, 2008, J.P. Morgan transferred the loans to the National Attorney Network for servicing of the loans (i.e., the right to collect payments from petitioner). The notification supplied to petitioner upon the transfer of the *252 loans to the National Attorney Network stated: "The transfer of servicing of your loan does not affect any 2012 Tax Ct. Memo LEXIS 241">*248 term or condition of your mortgage documents, other than terms directly related to the servicing of your loan."

The loans were eventually transferred to Litton Loan Servicing for collection. On August 24, 2010, Litton Loan Servicing mailed a letter to petitioner which stated: "Although this loan has been charged off, you still remain obligated for the repayment of the debt." The letter also indicated that petitioner had previously sent correspondence to Litton Loan Servicing on August 16, 2010.

Petitioner timely filed his 2007 income tax return ⁸ but did not file his 2008 income tax return until April 20, 2010. Both returns were prepared by an accountant working for MSLC Management, Ltd. Respondent issued a notice of deficiency for both years on March 11, 2011, and petitioner timely filed a petition contesting the deficiencies, penalties, and addition to tax.

Generally, taxpayers bear the burden of proving, by a preponderance of the evidence, that the determinations of the Commissioner in a notice of deficiency 2012 Tax Ct. Memo LEXIS 241">*249 are incorrect. Rule 142(a); Welch v. Helvering, 290 U.S. 111">290 U.S. 111, 290 U.S. 111">115, 54 S. Ct. 8">54 S. Ct. 8, 78 L. Ed. 212">78 L. Ed. 212, 1933-2 C.B. 112 (1933). Deductions are a matter of legislative grace, and a taxpayer bears the burden of proving entitlement to any claimed deductions. Rule 142(a)(1); INDOPCO, Inc. v. Commissioner, 503 U.S. 79">503 U.S. 79, 503 U.S. 79">84, 112 S. Ct. 1039">112 S. Ct. 1039, 117 L. Ed. 2d 226">117 L. Ed. 2d 226 (1992). Petitioner has not argued that respondent bears the burden of proof with respect to the issues discussed below.

Section 162 allows a deduction for all ordinary and necessary business expenses paid or incurred during the taxable year in carrying on any trade or business. The determination of whether an expenditure satisfies the requirements of section 162 is a question of fact. Commissioner v. Heininger, 320 U.S. 467">320 U.S. 467, 320 U.S. 467">475, 64 S. Ct. 249">64 S. Ct. 249, 88 L. Ed. 171">88 L. Ed. 171, 1944 C.B. 484">1944 C.B. 484 (1943). In addition, section 212 allows a deduction for all the ordinary and necessary expenses paid or incurred for the production or collection of income and for the management, conservation, or maintenance of property held for the production of income.

*254 Taxpayers are required to maintain records sufficient to establish the amounts of allowable deductions and to enable 2012 Tax Ct. Memo LEXIS 241">*250 the Commissioner to determine the correct tax liability. Sec. 6001; Shea v. Commissioner, 112 T.C. 183">112 T.C. 183, 112 T.C. 183">186 (1999). No deduction is allowed for personal, living, or family expenses. Sec. 262(a). Certain expenses specified in section 274 are subject to strict substantiation rules. No deductions under section 162 or 212 shall be allowed for, among other things, travel expenses, entertainment expenses, gifts, and expenses with respect to "listed property" as defined in section 280F(d)(4) "unless the taxpayer substantiates by adequate records or by sufficient evidence corroborating the taxpayer's own statement": (1) the amount of the expense or other item; (2) the time and place of the travel, entertainment, or use, or date and description of the gift; (3) the business purpose of the expense or other item; and (4) in the case of entertainment or gifts, the business relationship to the taxpayer of the recipients or persons entertained. Sec. 274(d).

Passenger automobiles and any other property used as a means of transportation are generally "listed property" as defined by section 280F(d)(4). Secs. 274(d)(4), 280F(d)(4)(A)(i) and (ii). Accordingly, with certain exceptions (none of which petitioner 2012 Tax Ct. Memo LEXIS 241">*251 has shown he meets), deductions for car and truck expenses must satisfy the strict substantiation requirements of section 274. The *255 heightened substantiation requirements of section 274 also apply to meals and entertainment expenses as well as travel expenses. Sec. 274(d); Bogue v. Commissioner, T.C. Memo. 2011-164, 2011 Tax Ct. Memo LEXIS 164">2011 Tax Ct. Memo LEXIS 164. at *50.

While petitioner did introduce some records and receipts for purposes of substantiating his claimed car and truck, meals and entertainment, and travel expense deductions, these items fail to demonstrate any business purpose of the expenses. Rather, the records provide only information regarding where the expenses were incurred and the amounts of the expenses. Accordingly, we find that petitioner has failed to prove his entitlement to any deductions for these expenses over the amounts respondent already allowed.

Section 162(a)(3) provides for a deduction for ordinary and necessary rental expenses incurred in carrying on a trade or business. However, petitioner failed to introduce any evidence that the rental expenses he deducted qualified as business expenses deductible under section 162. Petitioner likewise failed to introduce any evidence to prove the amounts 2012 Tax Ct. Memo LEXIS 241">*252 of any rental expenses actually paid.

Considering the foregoing facts and law, we find that petitioner has failed to prove he was entitled to deduct any of the Schedule C expenses in dispute.

The general rule is that "There shall be allowed as a deduction all interest paid or accrued within the taxable year on indebtedness." Sec. 163(a). Petitioner claims to have paid during 2007 and 2008 interest on six mortgages for which he was not the obligor. Respondent disallowed all of petitioner's claimed mortgage interest expense deductions for these six properties. In support of the deductions, petitioner has provided partnership agreements purporting to show that he owned a percentage interest in partnerships that managed ⁹ three of the properties: 21 E. Huron St. #2206, 21 E. Huron St. #2901, and 2428 Avalon Ct. No partnership agreements regarding the remaining three properties were produced.

The parties stipulated that petitioner made the following mortgage 2012 Tax Ct. Memo LEXIS 241">*253 interest payments for the three partnership properties: (1) $5,988 for 2428 Avalon Ct. in 2007; (2) $5,996 for 2428 Avalon Ct. in 2008; (3) $5,888 for 21 E. Huron St. #2206 in 2007; and (4) $12,423 for 21 E. Huron St. #2901 in 2007. In addition, petitioner introduced his bank account statements from 2007 and 2008 in an *257 attempt to prove he paid additional amounts of mortgage interest for these three properties.

Petitioner made no attempt to prove he paid mortgage interest for the other three mortgages—652 Nantucket Way, 704 Blue Ridge, and 243 N. Garfield—for which no partnership agreements were introduced, and we have found no evidence of such payments in the record. We therefore find petitioner failed to prove his entitlement to deductions for any mortgage interest payments for these three properties.

Even if we assumed petitioner made all the payments he claimed to have made with respect to the 21 E. Huron St. #2206, 21 E. Huron St. #2901, and 2428 Avalon Ct. properties (including and exceeding those payments stipulated), we would still find that he is not entitled to the deductions he claimed for mortgage interest paid for the three properties.

Although section 163 generally allows 2012 Tax Ct. Memo LEXIS 241">*254 deductions for interest on indebtedness, the indebtedness must generally be an obligation of the taxpayer, and not an obligation of another. Song v. Commissioner, T.C. Memo. 1995-446, 1995 Tax Ct. Memo LEXIS 446">1995 Tax Ct. Memo LEXIS 446, at *1995 Tax Ct. Memo LEXIS 446">6 (citing Golder v. Commissioner, 604 F.2d 34">604 F.2d 34, 604 F.2d 34">35 (9th Cir. 1979), aff'gT.C. Memo. 1976-150, Smith v. Commissioner, 84 T.C. 889">84 T.C. 889, 84 T.C. 889">897 (1985), aff'd without published opinion, 805 F.2d 1073">805 F.2d 1073 (D.C. Cir. 1986), and *258 Hynes v. Commissioner, 74 T.C. 1266">74 T.C. 1266, 74 T.C. 1266">1287 (1980)). Petitioner stipulated that he was "not the person named as the borrower for any of the mortgages."

An exception to the general rule that interest paid on an obligation of the taxpayer is deductible only by that taxpayer is found in section 1.163-1(b), Income Tax Regs. The regulation provides in part that "Interest paid by the taxpayer on a mortgage upon real estate of which he is the legal or equitable owner, even though the taxpayer is not directly liable upon the bond or note secured by such mortgage, may be deducted as interest on his indebtedness." We found that the taxpayer in Song was not entitled under section 1.163-1(b), Income Tax Regs., to deduct mortgage interest paid on a property because the taxpayer 2012 Tax Ct. Memo LEXIS 241">*255 was not the legal or equitable owner of the property. In that case a brother and sister entered into an agreement under which the brother would borrow money and hold title to a property, but the sister would have the "full responsibility" to pay the mortgage on the property. We held that the sister was not entitled to a deduction for the mortgage interest paid because she failed to establish that she was the legal or equitable owner of the property. We also noted that the agreement entered into by the brother and sister was questionable.

As was the case for the taxpayer inSong, we find that petitioner has failed to establish that he was the legal or equitable owner of 21 E. Huron St. #2206, 21 E. *259 Huron St. #2901, or 2428 Avalon Ct. No evidence suggests that petitioner is the legal owner of any of these properties, and he testified that his name was not on "the back of the title of the properties". Petitioner also offered scant evidence that he could be considered an equitable owner of any of the properties. It was unclear whether any of the properties had actually been contributed to any of the partnerships formed between petitioner and Mr. Hart or petitioner and Mr. Faruzzi.

Similar 2012 Tax Ct. Memo LEXIS 241">*256 to the agreement in Song, other aspects of the partnerships at issue in this case are questionable; petitioner failed to properly account for their existence on his 2007 and 2008 tax returns (instead treating the properties as if he personally owned them) and offered no evidence that any partnership formalities were ever followed. Considering the foregoing facts and law, we find that petitioner is not entitled to the claimed mortgage interest expense deductions for 21 E. Huron St. #2206, 21 E. Huron St. #2901, or 2428 Avalon Ct.

Section 164 allows a deduction for certain taxes, including State and local real property taxes, regardless of whether they were paid or incurred in a trade or business. Tschetter v. Commissioner, T.C. Memo. 2003-326, 2003 Tax Ct. Memo LEXIS 325">2003 Tax Ct. Memo LEXIS 325, at *2003 Tax Ct. Memo LEXIS 325">24. In general, taxes are deductible only by the person upon whom they are imposed. See *260 Tuer v. Commissioner, T.C. Memo. 1983-441, 1983 Tax Ct. Memo LEXIS 345">1983 Tax Ct. Memo LEXIS 345, at *1983 Tax Ct. Memo LEXIS 345">2-*3; sec. 1.164-1(a), Income Tax Regs. However, we have held that taxpayers who do not hold legal title to property but who establish they are equitable 2012 Tax Ct. Memo LEXIS 241">*257 owners of the property are entitled to deduct property tax paid by them for the property. Daya v. Commissioner, T.C. Memo. 2000-360, 2000 Tax Ct. Memo LEXIS 427">2000 Tax Ct. Memo LEXIS 427, at *2000 Tax Ct. Memo LEXIS 427">61; Trans v. Commissioner, T.C. Memo. 1999-233, 1999 Tax Ct. Memo LEXIS 269">1999 Tax Ct. Memo LEXIS 269, at *1999 Tax Ct. Memo LEXIS 269">21.

Petitioner did not hold title to the 704 Blue Ridge, 243 N. Garfield, 3010 Ilene, or 652 Nantucket Way properties. On his 2008 tax return petitioner deducted $14,419 in real property tax paid on these properties. Petitioner has offered no evidence that he was the equitable owner of any of the properties or that he actually paid the real property tax in question. ¹⁰ As a result we find that petitioner is not entitled to deduct the $14,419 in real property tax paid with respect to these four properties.

Respondent determined that petitioner failed to report $105,599 of discharge of indebtedness income for 2008, claiming that J.P. Morgan forgave the 2012 Tax Ct. Memo LEXIS 241">*258 debt that *261 petitioner owed to it after the sale of the 201 N. Westshore Drive #707 property. Respondent argues: (1) that petitioner did not dispute the discharge of indebtedness income in his petition and therefore the issue is deemed conceded by petitioner under Rule 34(b)(4); and (2) that the evidence and stipulated facts show J.P. Morgan canceled $105,599 of petitioner's indebtedness. We disagree with both of respondent's arguments.

Regarding respondent's first argument, Rule 34(b)(4) provides that a petition shall contain—

Clear and concise assignments of each and every error which the petitioner alleges to have been committed by the Commissioner in the determination of the deficiency or liability. The assignments of error shall include issues in respect of which the burden of proof is on the Commissioner. Any issue not raised in the assignments of error shall be deemed to be conceded. Each assignment of error shall be separately lettered.