Your original 1031 did not defer all your taxes.

I don't want to pay federal income taxes on the earnings I give them, the "interest" payout.

It's 2025, almost 2026, and everything in the tax industry is done remotely these days2 - waiting "a few months."

I don't want to pay federal income taxes on the earnings I give them, the "interest" payout.

I would talk to other tax sale investors or tax sale attorneys.

That’s insane.Protest your taxes people.

According to Airbnb:Guests who book Airbnb listings that are located in the City of Tuscaloosa, AL will pay the following tax as part of their reservation:City of Tuscaloosa Lodging Tax: 11% of the listing price, including any cleaning fees, for reservations 29 days or shorter.

You don't want to be in a position where you take a huge 401K withdrawal that it puts you in a much higher tax bracket where the added tax you would pay would be more than the added return you would get with real estate than whatever your 401K is invested in.Your net worth is about $1,500,000.What are your annual living expenses?

I've got an amazing Chicago property tax attorney that I highly suggest using. 

These are the exact areas I dig into as well, because they quickly reveal whether someone can realistically meet the participation requirements that drive STR tax benefits.Understanding W-2 demands, average stay length, hands-on involvement, and the dynamics with a property manager tells you almost everything about how the STR will perform and how the tax strategy should be structured.Most investors underestimate how much these factors impact both their numbers and their ability to use the losses.