Need help with possible trust?

I am probably in the wrong group for this but I have posted here before and got some tremendous answers. 

Here’s the situation. I have a friend in Florida who owns a condo and owes about 44,000 on the condo. Because of the relatively new condo law which requires the homeowners associations to charge fees in anticipation of a disaster repair, he can no longer afford to live there and I have been subsidizing him monthly to be able to remain at the location. We are both 75 years old. 

He has availed himself of an opportunity to apply for subsidized housing provided by a religious group that will allow him to live more comfortably and without assistance. 

That being said, they have conducted interviews and the impasse is that since he owns a condo, he is considered to have an asset of value and that takes him out of contention for the housing, even though can’t afford the condo payments.

I was thinking about setting up an irrevocable trust that would by the condo from him for what is owed on the mortgage and then it would become an asset not of him, but of the trust. Therefore when he is questioned about his assets he can honestly say he lives in a condo owned by a trust ad has no financial interest in it. Upon his demise, the trust would sell the condo and reimburse me or my estate as a trustee for what I paid.

One law firm discussed the 5 year “look back” and did not understand that I was referring to something other than medicaid. They were like a one trick pony.

First, does this question belong here?

Secondly, does anyone know if this is a feasible path to take?

Third, what if any pitfalls do you see.

Fourth,, when the condo is sold and the trust is paid, does that payment constitute income and will the trust need to file annual returns?

I thank you all in advance for the prior advice you gave me and for the anticipated advice on this issue.