The laws also make you register and pay hotel occupancy taxes, with some serious penalties if you try to not do either.Also, Airbnb doesn't work everywhere here.

I use them for 1040 prep, but that's it.Separately,  I have a Japanese CPA who helps with my J-taxes. 

I know of a Lawyer in Haverhill who will help apply for the necessary permits if this property is indeed able to be turned into a 3 unit.

DSCR loans are underwritten based on your credit, liquidity, and the rent you will receive vs the principal, interest taxes, and insurance.

As a newbie, my first question is around how to start out.What is the best type of business for Real Estate Investing to get the best tax break?

I agree with the cost of high taxes it's hard to make a profit but not impossible.

Keep your investment safe by talking to a lawyer, spreading your money around, and trying to have some say in how things go.

Multiple, billion dollar companies are investing into our area, such as Intel, Google, and Amazon, due to reasons such as lower costs on land, great tax abatement opportunities, and an attractive cost of living for employees.

However, I usually keep depreciation off the balance sheet until I can see the tax return and I go back and add it for the previous year.

Look at KKOS Lawyers.