I believe it can be liberated with the right approach and effort.The house is in Western Massachusetts.  

Because it's a bit of a liberal enclave, has an excellent school district, and there's no room to grow, I expect rental values to continue growing.

Or are some places more liberal with their valuations, etc...Would love to hear your thoughts.

Here is the guideline that is probably applicable to you to drop PMI without refinancing.Refinance. 80% LTV if SFR owner occupied will work.Note that while in theory it doesn't matter, generally appraisers are a little more liberal if the goal is just to drop PMI.

got to love Liberal Portlandia

@Brett Elia You've hit the jackpot with information by being right here on BP.

I am a pretty liberal guy, but anytime I am dealing with a TOPA issue I am cursing my own party lol.

How will you deal with a squatter or a legal tenant that refuses to pay rent in one of the most liberal, tenant-friendly states in the Union?

Do my numbers make sense or am I being too conservative or too liberal with any of them?

The day I left my JOB & decided to continue working for myself and building my company full time was one of the most liberating days in my life.