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My sense is that you're now in the exploratory stage, and will hire tax and legal counsel to hammer out the details if/when you proceed. Meanwhile, not a tax/legal consideration, but what jumped out at me was:
DS does not know that we are thinking about this...
Right now, he's a college graduate who's living independently, albeit quite frugally, which is typical for someone just starting out. What might it do to his sense of independence and accomplishment to be living in a house that Mom & Dad own, especially a fixer-upper where Dad's actually there sometimes working on it? What might potential partners think?

Admittedly I'm not at all objective about this. DD's ex-boyfriend has been living in, and acting as property manager for, his parents' house while they've been deployed overseas for several years. On paper, it looks great. In fact, he's in a rut, and my suspicion is that the house has become an albatross.

So, apples and oranges most likely, but I wanted to throw that out there FWIW.
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