Thanks all looking forward to growing some generational wealth. 

If you are going to pay for mentorship, find an experienced operator in your market or better yet, offer to invest in the experienced operators projects and get an inside look at their process and systems.

On top of that, hiring tribal members for construction or operations could qualify for employment-related tax credits.

You're operating under the assumption that none of your P2P borrowers default or are late on their payments.

The other is a smaller operation which does a lot of business in the specific neighborhood the house is in.

You also need the operating cash to do rehab.I say this because you mention FHA and low money.

Nothing wrong with LTR's - but what I like most about STR's is you are (usually) operating in better appreciating submarkets. 

The city operates on a block-by-block basis, and understanding those nuances takes legwork—or working with someone who truly knows the area.

If you're going to go that route with listing it, do it the right way or else you may find yourself in legal trouble, or a buyer may snake the deal from you.Again, novations aren't anything new, and most experienced investors are shying away from them these days because they're operating in a legal "grey area". 

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).