@Sarah Taylor From a tax perspective, you would lose the STR tax benefit if you expect paper losses from the property.

The title is still in the deceased name and there are some back taxes that need to be paid to clear the title. 

It can be HOA liens, tax liens, utility liens, etc.The thing that most people don't know about courthouse steps buys is that the same buyers are always there and they all know each other.

I would include at least the heavy hitters like title insurance, transfer taxes, appraisal, and paying my closing agent.

I bought a 5 acre property through the tax sale in June and finally getting title work finished.

Regarding Chicago, the 2024 property tax re-assessment in Cook County should cause some inventory to hit the market, specifically on the mixed-use and multi-family side of things which will be hit especially hard.

If they leave it to them in their will all the taxes go away.

In his opinion the best setup to minimize taxes was a checkbook LLC in an SDIRA. 

We have property taxes and insurance to pay.

I’m trying to have him see the bigger picture if he puts money in tax advantage accounts first and strategically uses a tax professional, that he will be able to offset his high tax bracket w2.