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Thanks, Ira, but it does feel like I'm getting scolded in some of the responses for even considering this. It seems that some folks are implying that I am forcing something down DS's throat because I haven't mentioned this to him, but the reason I haven't said anything is that first I'd like to know what is or isn't possible, and if I end up with finding nothing possible that meets my liking, I wouldn't want to disappoint him by first saying we were going to help him get a house, and then turn around and say 'never mind.' I see no reason to spin him up for something that might not happen.

Oh, no, you're not being scolded. Scolded is more like,
"Use your d@mn head for something besides a wig stand, will you!" Notice the subtle distinction?

I've been a CPA for 35 years, this fall. Telling people what they don't want to hear is not exactly a brand new experience.

And beyond taxes, your topic's OP stated what might be its biggest drawback:

"We have multiple goals here - helping DS to get a good place to live that is affordable to him, getting our retirement home, and possibly picking up some investment property along the way. These are in rough priority order.

Well, your multiple goals are in conflict, beyond it being a matter of priorities. And you need to get REALLY CLEAR about which it's going to be, for DS's sake. Is he going to end up being a homeowner, or just the interim resident caretaker of your future retirement home? That little question needs to be nailed down solidly, before you get into a convoluted ownership/rental arrangement.

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