We've come to realize that the Boston market is too tough and the numbers don't make sense (to even house hack), so just recently, we decided to hone in on Plymouth, MA... with the idea that it could be a good tertiary market to do furnished rentals (thinking short-term/AirBnB in the summer, and mid-term in the offseasons).

This strategy could help him boost retirement income while avoiding capital gains taxes, but consulting a tax professional or 1031 specialist is essential to navigate the process correctly.

STR is becoming a difficult strategy because there are so many costs (furniture maintenance, utilities, internet, etc.) that you have to factor in and if you are in an oversaturated market, then unless your property is unique, you can only compete on price.

These property management companies have their own Lawyers, If they paid me back they knew they are Foul playing, I play by rules and Expect the same from others , and I don't agree with people who are siding with wrong side and attacking back and also taking their grudge on others is far from being Professional rather they should not be in the jobs where they donot have patience

The market is surprisingly high here for such a small place, but i think its because the town in growing and has a very good school system.

In today's market, what innovative strategies are you using to maximize ROI on properties that might traditionally be considered high-risk or low-yield?

I'd say first, figure out what kind of investing you're into and make sure that the market you choose supports it. 

I’d rather trust a professional with a moisture meter to see if it’s dry (just after or even during a heavy rain would make me feel better) before fixing the ceiling.

There is definitely more options for investing opportunities on the open market than on the land bank. 

As a general rule, it's best to learn how to handle problems before they become problems. make a list of the potential problems you could face as a landlord: rent rates, marketing, collecting deposit, late rent, unpaid rent, abandoned rental, early lease termination, unauthorized pet, etc.