I am not trying to deal with a bunch of metal keys or 12pm lockouts.

Your last conversation should be pay or leave..Your last resort will be to offer cash for keys..

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.

You are better off analyzing the remaining life of major Capex components like roof, windows, plumbing, furnace, AC and have a reserve fund set aside as part of acquisition cost.

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).