You might get transferred a couple times until you reach the right person.

There comes a point where having a real estate-savvy tax preparer outweighs your time learning a new software. 

Personally I consider it to be more of a entry level neighborhood for first time home buyers and a blue collar neighborhood for long term renters.

In fact, some lenders add back repairs that are "one time" repairs.

You might want to get in touch with @Andrew Freed and Jonathan Bombaci, they are locked into several of the MA meetups which are great ways to connect with other investors in real life.

I would suggest starting with reading the IRC book all the way through multiple times.

You said you've owned the property for 8 years; that's like 2017 which was a prime time to buy.

Unfortunately this market doesn’t appreciate that quickly, but I possibly may do that in 2-3 years depending on the market, debt pay down and the interest rates at that time. 

However, if it is an STR, the depreciable life would be 39 years.

Sorry to say but it's time to lawyer up.