If I need to take a months' unpaid leave to help them around the house, cleaning, cooking, caring for their daily needs, it won't be a big deal.  

But if your main goal is to make money while minimizing headache, then the returns of this are marginal at best, as @Julie McCoyand @Ethan Cooke mentioned.If you had a two bedroom house, maybe you could do it so that you help out your friend and you can always get a room filled in Denver metro on Airbnb.

You're paying to not have to cook or clean. 

@Frank Sanchez - I knew the taxes were high in Cook County but I didn't realize it'd eat into it that much - good to know.

The driveway has concrete walls on each side which prevent the gravel trucks from delivering and spreading it for me, trust me, I didn't want to do this lol.Today was landscaping and some little things such as trim work and some work on natural gas pipes (putting on shut off valves, connecting the cook stove, etc.)

I think last time the consensus was don’t rent to them if they cook with a lot of spices.

He also eventually stopped paying rent because he lost his job as a cook due to an argument with his fiancé.

No new clothes or shoes and learn to cook.

This presents a situation where were looking for a niche tenant - someone who can afford to buy a home but has life circumstances leading them to rent and who also does only minimum cooking or eats out a lot.

Quote from @Jay Hurst: Quote from @Todd Bentley: Quote from @Aaron Kerwin: I talked to my lender at Castle & Cooke in Denver, CO and for them, the seller now turned buyer would just have to show that the existing loan was being paid by someone else for 12 mths and they won't count it against their DTI.