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

Taxes? 

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. 

Looking for a CPA or tax preparer that is well versed in the STR loophole and cost segregation.

Below is a quick summary: Generally, the four sources of return in rental real estate are:1- Cash flow2- Loan paydown3- Appreciation in value4- Tax savingsExamples of performance metrics and what they are designed to measure:- CoC (Cash on Cash) is a measure of net return generated by TWO sources (i.e.

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.

Also seems like they like to stick on wealth taxes for rich greedy landlords and investors.

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. 

WC is great - great schools, lower taxes.