Having two people paying rent, but only one living in the house is not ideal unless both understand clearly they are liable. 

You should also be aware to make sure what was provided does or does not meet industry standards.

I would echo what others have said - 100% start locally because you need to gain an appreciation for what it means to be an investor, understand the lifecycle of a deal and be on the ground to observe what's going on with renovations etc.

It is my understanding that a CPA is only responsible for making sure you follow all the laws when filing taxes, but there is another role that is responsible for tax strategy and focuses on tax savings. 

I self-manage, but I understand that's not a practical option for most people.

We managed to navigate it, but it was a lesson in the importance of understanding both federal and state regulations.Given your location in Boston, Massachusetts, it's especially pertinent to consult with a qualified intermediary or tax professional familiar with both federal and Massachusetts state laws to ensure a smooth exchange process.

The biggest advantage of using someone local to where you're buying is that they will understand taxes, insurance, and similar items very well when it comes to DTI/DSCR calculations and payment quotes, and they will likely have a local network of service providers for ancillary services (survey, inspections, etc).

I do understand that market value becomes what has been paid for a deal but with minimal work and renovations my deals almost always significantly increase in value in the first 6 months.

Start by researching areas that fit your goals, understanding financing options like FHA loans, and using the 1% Rule to evaluate deals.

We were able to get standard mortgage financing How did you add value to the deal?