Experience can be the difference in structuring a deal to make it work and ultimately acquiring the property successfully.

Also, you'll need an architect and engineer inspections to make sure the structure is safe. 

I think the other commentators have it right - a HML that is willing to take an investment that is small is probably not vettable and not a smart play - however if you have ~$500k or more to put in, then the legitimate more easily vettable firms would pottentially be interested - and you would be able to see the sophisticated setup, documents, structure etc and be able to research accordingly

I would think, and this has been confirmed to me by several estate and elder law attorneys; as well as tax attorneys, that a tree structure where you have a parent LLC and then wholly owned sub-LLCs under it's umbrella is the correct way to do this. 

Why would the basic structure of a subject to transaction be different in Illinois than it would in any other state?

I've been told the answer is to set up a revocable land trust with the LLC as the beneficiary of the trust and an appropriate trustee structure.

@Jacob ZivanovichPartnering with someone who can co-sign your loan can be a great way to get started with your house hack, provided the partnership is equitable and well-structured.

Sometimes sellers are very structured, controlled, and follow the rules to the letter, but sometimes they may not be as smart.

Consult a structural engineer for other material choices.

Identify high quality opportunities (homes with good foundations and structure that will last 30+ more years)4.