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.

If your income is transferable, you could get back on your feet much more quickly by moving to cheaper, less competitive market out of state.

Therefore expect a 15 page home inspection report   filled with corrective measures you must satisfy otherwise the buyer walks.All in between turning over the home, ordinary transactional costs ( broker fees, transfer tax, loan payoff fees etc.) seller assist, repair addendum repairs its very possible for your exit fees to approach 13-15% of the properties sale price. 

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

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

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.

Usually an appraisal can be transferred to a new lender, so as long as it wasn't completed 90+ days ago, it should still be valid.