My CPA has essentially called it a "tax asset" - where you end up w/ tens or hundreds of thousands of dollars in losses that have been passed forward so that at some point you can offset passive gains. 

If I’m wrong we lose potential equity gains.

If you consider going north, the Manchester market has been seeing some extraordinary gains (similar for RI, though).

I’m brainstorming ideas on how I can market myself to potential mentors in the STR game in order to gain experience.

You're gaining equity.

I've got something to gain.

To maximize my cashflow and gain landlording experience, I’d do STR and MTR in the other units, as well as the other bedrooms in my unit.

By purchasing a multi-unit property, living in one unit, and renting out the others, you can cover your mortgage payments and start building equity while gaining rental income.

You pay on those gains. 2.

I'd sell because you are reaching the time when you lose the cap gains exemption and that $24K would take over 2 years of renting to get back.I had a condo that I owned for a long time and I sold it despite it being paid off and having long term tenants.