I personally like Alabama and Tennessee a lot, depending on what specific area you're looking at.Look for Class B or C properties in stable rental markets, particularly single-family homes or duplexes.

Some of the heavy hitters here in Chicago discussed the ADU program with a very nice person from the building department.

Quote from @Daniel Windingstad: Quote from @Obed Calixte: Some people have the personality, processes and systems & time to self manage, some do not.

Personal Guarantee: Will you require this?

Here’s a breakdown of the main ways investors fund their first deal while minimizing their own cash outlay:1.Private Money & Hard Money Loans– These lenders focus more on the deal than on your personal finances.

So it's just personal preference and budget for a host.

Our short-term residential investment property loans are typically 60-80% LTV and all are personally guaranteed by the borrower(s) -- we pull credit, background and PFS on each guarantor, verify experience, verify liquidity, underwrite the property, neighborhood and zip code.

Id have a lawyer on hand, this person seems like they will escalate issues once you notify them you aren't renewing their lease.  

This is basically a math problem that will depend on both you personal finances & also how much of this is an investment vs you want a nice house to live in4.

@Sonya Sharova I haven't personally done Frank Rolfes boot camp but I have heard it's great.