No insurance, twice

How about if he did not itemize at all in 2019? Just not enough charity, taxes, interest.

Here are a few things about the Pub.

Sale of Medical Equipment or Property
If you deduct the cost of medical equipment or property in one year and sell it in a later year, you may have a taxable gain. The taxable gain is the amount of the selling price that is more than the adjusted basis of the equipment or property.

. OK, but we did not deduct it in any year.

The adjusted basis is the portion of the cost of the equipment or property that you couldn't deduct because of the 7.5% or 10% AGI limit used to figure your medical deduction. Refer to your Schedule A for the year the cost was included to determine which limit applied to you. Use Worksheet D to figure the adjusted basis of the equipment or property.

. OK, but the 7.5 or 10% was not why we did not deduct it.

Worksheet D. Adjusted Basis of Medical Equipment or Property Sold

Instructions: Use this worksheet if you deducted the cost of medical equipment or property in one year and sold the equipment or property in a later year. This worksheet will give you the adjusted basis of the equipment or property you sold.

. OK, but as I said, we did not ...

Worksheet E. Gain or Loss on the Sale of Medical Equipment or Property

Instructions: Use the following worksheet to figure total gain or loss on the sale of medical equipment or property that you deducted in an earlier year.

. OK, same comments.

So where does this leave us? We're golden, right? None of that applies, so we keep our basis. If we sell in 2020 for its then fmv, 12k, we have a non-deductible personal loss, I guess. (Or, if somehow that thingy about basis becoming the lower of cost or value at date it went up for sale, which I think does not apply, a breakeven.).

Not so fast. I'm not even sure the wheel chair retained its characterization as a capital expenditure. That reg. I cited way back, 1.213-1(e)(iii) says

(iii) Capital expenditures are generally not deductible for Federal income tax purposes. See section 263 and the regulations thereunder. However, an expenditure which otherwise qualifies as a medical expense under section 213 shall not be disqualified merely because it is a capital expenditure. For purposes of section 213 and this paragraph, a capital expenditure made by the taxpayer may qualify as a medical expense, if it has as its primary purpose the medical care (as defined in subdivisions (i) and (ii) of this subparagraph) of the taxpayer, his spouse, or his dependent. Thus, a capital expenditure which is related only to the sick person and is not related to permanent improvement or betterment of property, if it otherwise qualifies as an expenditure for medical care, shall be deductible; for example, an expenditure for eye glasses, a seeing eye dog, artificial teeth and limbs, a wheel chair, crutches, an inclinator or an air conditioner which is detachable from the property and purchased only for the use of a sick person, etc.

. To me, it's inconclusive:
It's a capital expenditure made by the taxpayer and it meets the other stuff, so it "may" qualify as a medical expense. In the very next sentence it says that if it otherwise qualifies as an expenditure for medical care, which it clearly did in 2019, it "shall" be deductible.

So, is it a capital expenditure that retained its basis, or
a capital expenditure that, because it qualifies as a medical expense, may, or shall, be deductible, but either way became an expense, not a capital expenditure, and
If an expense, is its 2020 sale treated as Pub 502 treats reimbursements in a later year or reimbursements you didn't deduct?

What if You Receive Insurance Reimbursement in a Later Year?
If you are reimbursed in a later year for medical expenses you deducted in an earlier year, you generally must report the reimbursement as income up to the amount you previously deducted as medical expenses.

However, don't report as income the amount of reimbursement you received up to the amount of your medical deductions that didn't reduce your tax for the earlier year.

For more information about the recovery of an amount that you claimed as an itemized deduction in an earlier year, see Recoveries in Pub. 525, Taxable and Nontaxable Income.

What if You Are Reimbursed for Medical Expenses You Didn't Deduct?
If you didn't deduct a medical expense in the year you paid it because your medical expenses weren't more than 7.5% of your AGI or because you didn't itemize deductions, don't include the reimbursement, up to the amount of the expense, in income.

Is it a "recovery"? https://www.law.cornell.edu/cfr/text/26/1.111-1
Is it a reimbursement? viewtopic.php?f=8&t=19709
Or is it just a plain old sale?

Or did today's Eagles' loss just screw up my mind?

Sounds to me like the homeowner's insurance is trash, and he needs a lawyer or a lower deductible and better insurance. lol