What is the best way to handle this for 2019 while also not creating a headache for myself for 2020 when the unit was sold?
Do not convert the property to personal use. Leave it classified as residential rental real estate. This makes it simple to deduct your repair expenses as rental expenses. Repairs paid for in 2019 would be deducted as such on your 2019 return. Repairs paid in 2020 would of course be deducted on the 2020 return next year. While shampooing the carpets is a maintenance/repair expense, the "new floors" might not be a maintenance/repair expense. That might be a property improvement. But it depends on exactly what you mean by "new floors". So you'll need to elaborate on that.
Now there are going to be those who will say something along the lines of *you have to convert it to personal use because....." and technically from a legal standpoint they're not wrong. But I view it like this:
If I owned a SCH C brick and mortar business and closed the doors permanently and forever for that business in Nov of 2019, then sold it in 2020, I am not going to convert the building to personal use between the time I closed the business and then sold it.I'm selling the business, and will report it as the sale of a business.
Rental property is a business too. When I decide to no longer rent it out and sell the property, and I actually do sell it within a reasonable amount of time after the last renter gets moved out, I'm still selling rental property.
Besides, it's not like the IRS is going to single you out among the tens of thousands (if not more than a million) rental property owners that sold their rental property in 2019 or 2020, unless you give them a reason to single you out.
Since there's no question the property was rental through the end of November (since rent was paid for that month) leaving it classified as such until yo sold it will only result in 4-5 months of depreciation. Based on the the total depreciation already taken on the property I seriously doubt it's going to make enough difference in your tax liability to make the conversion headache worth it.
Now if this was a case where the last renter moved out in say, April of 2019 or earlier and you didn't sell it until 2020, then I"d say convert it to personal use on the 2019 tax return. Then on the 2020 tax return you'd report it as the sale of a 2nd home that had prior business use. That's a PITA. But keeping it as a vacant rental for 8 months or more prior to the sale may raise flags. I don't know for a fact that it would though.
