Hi Jason,Here's a few things I'd be mindful of:Separate Personal and Business Finances - get an EIN, open business bank account and use it exclusively for businessMaintain Documentation - keep records of all business transactions and contractsComply with Legal Formalities and Tax Regulation - adhere to all state specific regulationsIn terms of the STR and LTR, it's generally recommended to put them under an LLC by transferring ownership or quitclaiming.

There is a big distinction on the variety of restrictions you need to be aware of with ADUs in Chicago specifically.

Specific to payments, try to push for net 30 payment schedules for your GC.

Alternatively, using it as a homestead for your child has tax benefits, but rental income might be limited.

Let me know if you have any specific questions about Nashville and the surrounding area. 

Alternatively, explore conventional loans with higher down payments for potential flexibility and lower rates, or check out private lenders for more complex projects.

While I initially bought my first property outright with cash, I'm interested in alternative approaches.

Option 3 may work in the specific location as well, as its "up and coming."

@Derek Todd McCarley if you have $1m in capital gains this year it's worth it to pay several thousand to get some solid tax advice. .Without the specific background on how this $1m in cap gains was generating it's tough to provide helpful feedback but you can explore 1031 exchange, 121 excl, Qualified Opportunity Zone, and more 

I’m actually possibly the final fed defender, I think overall Powell has done a fantastic job, kept the ecconmy afloat during Covid & yes we paid for that with inflation but I think the alternative scenario’s were just much worse, he probably should have hiked rates like 6 months earlier but regardless got inflation mostly under control, now he’s signaling a piviot and the economy still seems on fairly firm ground, even the mortgage rates which are slight beyond his control have been great, this last 18 months have definitely been extremely restrictive rate’s which the housing market absolutely needed to ring out the rampant speculation, seems like this year rates will be mildly restrictive which is what you want to avoid reheating the economy/housing market.