This is sort of a long read and not exactly a simple situation, so I apologize in advance.

My current situation: I owned my house outright, until I got divorced last year. I needed to pay off my ex in the settlement, so rather than letting her raid my retirement I took out a 3% locked in HELOC for $100k. Total payment is almost $700/mo for 15 years. I wanted to sell this house even before this happened, but now I'd really like to erase this debt that just reminds me of what a **** she is every month when I see it coming out of my account.

It's rural so I also want to move closer to civilization as well. I still have over $116k of credit left on my HELOC, should I need it.

My son's situation: He just got a great job, union steelworker in a nearby town. 18 years old. He's very responsible with money, I taught him well. He was interested in buying his own home soon so he could have it paid off before he's 50. The problem with that is, he cannot get a mortgage until he has 2 years of work history. He started this job a few months ago so he has a lot of time to go before he's eligible. I could co-sign, but I don't want that mortgage to affect my DTI going forward. OTHER IMPORTANT INFO: His mom passed away when he was 5, and he has some significant (> 6 figures) of money from her invested in mutual funds earmarked for him BUT... all of it is in my name right now. He was completely unaware of this money until he wanted to buy a home (a few weeks ago), and I decided to tell him about it. Transferring the money to him when the time was right has always weighed on me because of the tax implications.

When he said he was looking at homes, he was looking at homes that were easily affordable at his wage level. But... it occurred to me... that I can gift him (currently) $16k/year tax free, which comes out to about $1300/mo. He could absolutely use that for the house payments, get a nicer house than what he thought he could, and he wouldn't have to pay that much out of his salary for many, many years. Plus I'm not dropping a windfall on him that he might be tempted to spend frivolously (though he's not likely to do so anyways). And of course, the money will continue to grow in the mutual fund portfolio even as I gift to him out of it.

He found a home that he likes, near his work. It's a place I wouldn't mind staying in for a bit. What I am thinking, is that I could buy that house and then in 2 years he could get his own mortgage and buy the house off of me for the price I paid for it. By then I will have been able to have transferred him $48k in tax-free gift money from his earmarked account that he could use for a downpayment without having to stretch his regular wages. Additionally, the $1300/mo will almost certainly completely cover his mortgage payment for the home. He may even be able to do a 15 or even 10 year note. If I buy that house and use my remaining equity from my current home sale, I should own that new house outright, or very close to it, right away. It is a 3 bedroom house, so I can live there with him until I decide to get my "own" house.

Even if I decide to move before the 2 years are up (I'm looking at Florida), it won't be bad because I'll have no debt and will be able to pay for another house if I move out and he takes care of the taxes and such on this new house he's looking at. I'd need a downpayment, but I have investments I could pull from (not ideal but possible) that I could leverage for that.

What I'm mostly wondering at this point is if I should consider a better way to structure this to minimize transfer costs in 2 years when it's time for him to take full possession. I'm thinking of protection of his assets in case of future marriage/divorce, minimizing transfer fees, etc. Anything that should be considered. I'm wondering if some kind of trust or similar might be worth looking into. Though it might be difficult for him to get a mortgage for a home that would already be in a trust that he's a beneficiary of to "buy" the house from me?

Should I just buy the house in my name completely, and then have him take out a mortgage and buy it from me FSBO as soon as he can? Straight, simple, to the point? Or is there some creative way perhaps that I could improve upon that?

The new home, even as a temporary measure, will be beneficial to me now, as well as to him.

- Getting rid of that HELOC from the divorce (mostly psychological but will enjoy the return of my cash flow)
- Completely shedding the remnants of my marriage (admittedly psychological)
- Downsizing from a big house that we don't need to something more reasonably sized and easier to maintain
- Getting me, a middle aged single guy, closer to more activities and socialization prospects
- Much, much closer to his work, and to stores etc. It'll drop commute costs way down. I'm remote, so that doesn't matter that much to me.
- Getting him into a house as soon as possible so he can have it paid off (or have enough equity to leverage it for more investments) sooner rather than later

Pittsburgh, Pennsylvania

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