It's awesome to hear how aware you are about the transferability of your skills to real estate! 

If you are closing on a property that you will reside in, can you close it in a Trust, or do you have to close it in your own name, and then later transfer it into a Trust? 

Worst case you can transfer the money from the current custodian into Fidelity and back and forth it would just create work for you and possible wiring fees....

This seems like a lot of work to save 15% of $35k in taxes (Less than $5k.) especially if you have transfer taxes or title insurance, or you convert your long term 15% rate in to your son’s regular income tax bracket.I hate paying taxes as much as the next guy but this lemon isn’t worth squeezing.

I would just pay off the arrears, pay out your equity, and transfer title. 3) Sell on the market, but then you'll lose some of that equity in closing costs and commissions. 

@Sam Rogers A Deferred Sales Trust (DST) allows you to defer capital gains taxes by transferring sale proceeds to a trust in exchange for installment payments, offering tax deferral and reinvestment flexibility beyond 1031 exchanges.

Eventually, I would like to transfer the property to an LLC. 

I know you said why but I mean, what does actually transferring the units accomplish? 

Understand Proposition 13 for property tax benefits, local transfer taxes, and strict tenant and rent control laws.

Ideally there'd be second factor requirements on any transfer, and especially "suspicious" ones (as defined by an entire team of people who monitor that sort of thing).Cookie theft and other takeover scenarios are a thing.