Based on your situation, you will likely need to recapture the depreciation when you convert the property from a rental (STR) to your primary residence in 2025. 

We simply include the tax on the invoice sent to guests, which makes it easier to track and ensures we're covered for tax purposes at the end of the year.For Chicago, I’d recommend checking directly with the city’s tax office or a CPA, but generally, you’ll need to register with the city, collect the hotel tax from guests, and remit it on a regular schedule (likely monthly or quarterly).

Are you sure you can add 2,000 SF on such a small lot? 

I didn't negotiate a ton on price as the deal seemed pretty reasonable.

The InvestRE360 Mastermind will meet on the 29th at noon in Idaho Falls, the East Idaho REIA will be February 19th in Idaho Falls at TitleOne at 5:30pm, and the PokyREIA in Pocatello should be the first Tuesday in February. 

My CPA was unsure... do you issue 1090-NEC for the difference between 1099-K and 1099-MISC or do you double up the income (i.e. 1099-NEC for gross rents from PM, 1099-K of the net owner distribution on 1099-K, then owner reports double income and puts a line item expense for the 1099-K since 1099-MISC covers gross rents).You need a new accountant lolPM issues 1099-MISC, not NEC for rental income paid to property owners.You would still issue the rental income paid to the owners regardless of the payment method.The Property Owners should add an expense line item on Schedule C stating that income reported twice on Form 1099 to offset any duplicated amount.

This would apply to your unit.Your biggest concern with setting the rent should be the near future. 1) Your insurance is guaranteed to go up, probably dramatically.  2) You may get an insurance assessment bill to cover the CA Fair Plan losses.

The rent from this property covers the mortgage.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

Can you speak on how you source granite slabs cost effectively?