I have talked with several clients who have had a similar thought process - in their mind almost a "block chain" for the real estate investment.Along with the SEC regulations regarding investment offerings, the IRS has neatly placed this "blockchain" type idea as being a tax partnership. 

The first two ideas would be rent by the room and/or making it a mid term rental if those make sense. 

This will give you an idea of the average sale price and what you can expect to get for the property if you make the necessary repairs and upgrades.Property History: Look into the property's history, including any previous owners, liens, or legal issues.

You can call your the local utility company to get an idea on utility costs.

@Devin Dang any ideas?

I have already secured renters and am very excited to get started.Regarding the Chicago market, I have come to understand that there is an abundance of multi-family properties, but it is important to note the property taxes outside the city limits can be very high.

Not always a good idea to just use the same vendors as the seller as there may be improvements you can achieve. i.e. property management company doesn't give guests the easiest instructions to check in, so reviews are down. 

The prior history was there before to indicate it was a bad idea, but she rented to them because she felt sympathy for their situation.

However, I have another property that puts me over the $750K limit. 

It's the same request, but one is higher intent (or at least appears so... a verbal statement that "I want to buy 123 Main St" does not obligate you to anything), and one makes the request for more information THEIR idea.