I think once you get more than that, you would need a more expansive program

All of which nothing will help him because the loan is still in his name. 

Far more costly to transfer property at a later point than simply purchase in an LLC on day one.

Happy to help point you in the right direction and give my insight if you want to shoot me a message.Best of luck!

To help avoid a lot of these issues I would think about buying a "Modular" or use a "Tiny Home" vendor who offer these in many states.

I wish there were more stories like yours out there.

House hacking is financially a no-brainer and no city in the US (including Chicago) has more duplexes than Milwaukee.

I have 6 condos here and will likely be buying some more property soon.

So, you can do a land contract for 12 months, which should allow lender to credit you full value of the land vs the purchase price, but the loan will pay off the land contract, so the lender maintains first lien position.Can't help you with the rest of your question, but you should be able to search for "CPA" here on BP to find experts to reach out to.

@Jason LopezIf you only have one rental or a few I would worry more about how to get more vs trying to put each one in an LLC.