Put yourself in their shoes.  

In the case I mentioned above, there were special circumstances of the sort @Rion Redinger mentioned.If I were in the tenant's shoes, I would feel deeply insulted if I got a "gift" from my landlord.

In times of a cash crunch not many want new clothes or shoes.

@Joanna GoldenThere are certainly private money lenders and hard money lenders that will do these kinds of loans, but my personal opinion if I were in your shoes, would be to stay far away from them if at all possible. 

Then, I did more research and the family was worried about the tax consequences of doing all straight sales and changed our plan to trading these wildly appreciating condos for true Multifamily and more cash flow to help us to be financially free.More education by reading, attending an excellent 2 day workshop, and talking to many people that had been in my shoes at one time, we chose this current route.  

If I’m in your shoes I’m probably going the condo route, the biggest targets for you right now should be subsidizing your housing costs as much as you can and safety.

That is, say they need a wheelchair, you can accomodate them by allowing them to install their own ramp, but you aren't necessarily required to build it yourself.Might be wise to brush up on the Fair Housing Act and chat with a lawyer to understand the nuances in your particular area.If I was in your shoes, I'd ask: "Are there any legitimate reasons I might not want to rent to this person (credit, evictions, felony, etc...)"

@Jean SooI was in your shoes recently w purchasing a house this year in March and had to rent it out in April.

You have the Contract and you are the Owner; if I were in your shoes I would let him know that if he fails to pay, you will start eviction proceedings. 

If neither of these make sense to you give me your input on what does make sense in my current situation if you were in my shoes?