One odd question- can he show a picture of his 'Key Room'?

I think the key here is to look for value-add condo in a prime area of Chicago. 

Build a Duplex, fill with tenants and sell as a turn-key property to an investor.3.

Also, I'm not saying it was a good or bad decision, but if you bought a house that needs work, by definition you did not buy a turn-key.

The key is to choose the one that is best for your situation, skill set, and temperament.

My first questions to get answered are always:-  Do they have an existing mortgage or do they own the home free and clear (if a mortgage is present, do they need to pay it off for the deal to work)- Do they need the cash or do they want a prolonged income streamAnswers to those questions can help understand some of the key seller motivations.A typical seller financing structure would have a down-payment that would range from $10-$20K up to 10%-20%.Interest rates typically range 1-4pts over residential real estate mortgage interest ratesIf the seller wants long term cash-flow, the term can be 10yr-30yr.   

The long-term tenant probably has a higher chance of staying, but it would be much easier for me to have them move, vs. having to buy-out the current lease of the June 2019 tenant (or do cash-for-keys).

I used to use padlocks, but it‘s expensive up front and also re-keying when keys get lost, and I had to meet with tenants to provide the key.

They are planning to give us the keys at the move out inspection even though the lease explicitly states that keys must Be returned within 24 hours of lease end.

The key is to find a local commercial lender who understands your business and sees the value.