This has to be one of the least friendly states to be a landlord, and the taxes are high.

Taxes? 

Helped us pay off the mortgage, now we are paid to live here after paying all expenses like taxes, insurance, utilities,  internet,  etc👍 

So just knowing the basics and directing them in the the best tax position is helpful.

This will help you stay organized and make tax filing easier.8.

Have considered bank note investing, tax lien/deed investing, loaning it out, etc. 

And fun fact, most states exempt groceries from sales tax, (again, actual groceries that are whole food, and not processed).

Before going into this, though I would be very conservative in your analysis of cost to renovate and what you think market rent (along with increases in taxes and insurance) would be so that once you are ready to refi into a longer term loan, your DSCR is rock solid and so is your cash. 

You can also explore Salem or bordering areas such as Derry or hereabout but they tend to be very high tax areas so that eats away quite a bit of returns and would not appreciate as well as more Boston central locations.

What happens if you inherited the longevity gene from your great aunt Mary, and you live to be one hundred years old?