I live in CT but am interest in determining if over the boarder in Wester MA is a better territory to invest in BRRRR.

They can determine what to pull out of each of our comments.  

This will make it easier at the end of the year for you to quickly determine what is a business deduction.Accounting Software Recommendations - Quickbooks(Desktop), Quickbooks(Online), Stessa, XeroOnline Storage to save receipts recommendations- Google Drive, Dropbox, Apple DriveExcel - to save information such as tenant name, lease start date, current rent, etc

Your lease should determine this.

Seems I need to figure out how I want to invest to determine the best mentor, right?

I'm not trying to speculate the market in the future, I'm more or less trying to determine if the move is smart ..

In order to minimize these taxes, it is important to make sure that all of your assets are properly documented and organized so that you can determine what would be best for your heirs.

@Mike Schorah Hey @Mike Schorah I respect your determination and drive.I always encourage people to invest their time into going out and meeting investors in your market.

That will help determine the best course of action. 

I work with many licensed folks who do just that, their message being basically "I can buy for this or list it for that" Even if you do not work the listing yourself, you should be able pass a listing to someone else, split commission and get paid legally.Now your task will be finding people who want or need to sell their property, triaging the best solution for each, make your offer and use the appropriate paper to get the job done.In this process, you'll come across those deals you can cherry pick for yourself once you determine your own buying strategy and holding criteria.Each step can be planned and executed according to your investment plan as @Amber Forkey suggested.Hope that helps