If anyone is familiar with massachusetts, the areas vary widely- cape cod, new bedford, taunton, south shore, and of course boston itself (out of my league d/t price) are all much different in price/rent ratio, schools, crime, etc... what are the things that matter most to you and influence your decisions when looking into different markets?

Just be careful and go in eyes wide open and run your numbers.

There is a double-wide trailer on the property as well which rents for 550 and is currently occupied, same tenant would like to stay when property is sold. 

I know it's typically not great.I realize this is a wide open question, but I enjoy people's opinions on this board - any thoughts on paying down the balance of the rental to keep it cashflowing versus just buying a 3rd property?

It varies widely depending on the process, the workload, and what you're trying to do.

It can also widely depend on how closely you want to manage the managers. 

I cut a 6 feet wide opening that leads into the kitchen.What say you folks?

The entire floor is already/will be 3/4" 2-1/4" wide oak hardwoods (everything but the bathroom).

Also, quite frankly, I don't really know what I want to do for a living and have been exploring some real estate related career paths (Loan Officer and Broker mainly but my eyes are WIDE open).

Looks like notation wide Atlanta come 1st in high water charges.