I'd be happy to talk with you further about how to leverage your real estate license in pursuing your investment goals.

I'd consult a bankruptcy attorney and a good commercial insurance agent.

If such tax law prodigies exist, I’d love to meet them.

I'd also worry about the showings and if someone steals something from the tenants (or the tenants claim something is missing).Focus on getting the most you can for the property.

I would imagine most attorneys located around the MA, NH border area plan to make more than $200,000 per year.

I'd love to source from Craigslist and FB like @Michael Baum but have often struggled.  

Being out three months of rent plus $1,500, I'd be better off handing back their SD and forgiving the month of rent they couldn't pay.  

I know you want to go full time and jump in, but I'd recommend staying with your day job as long as you can - it makes your life a lot more comfortable to have a steady stream of income to pay the bills every month!

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. 

I’d greatly appreciate any insights or experiences you could share on this topic.Thank you again for your help!