Massachusetts has a ton of opportunities, so let's search for the right one together.  

If the seller's attachment to their home exceeds their desire to make money on it at this time then no sale is going to happen.

Kevin R Moses - search for house hack or house hacking and read Set For Life.

I found out what I needed to know after doing a title search.

Might take some searching, digging, time and patience, but you've got this!

To find a good deal, you will most likely have to do some leg work to beat out other investors also searching in your area. 

@Dara Kharabi I hear baltimore is being built up and is ideal for flips, I have yet to have my wife do some searching on the MLS but she's talked to other investors and has been given the heads up about the market out there.

You haven't searched.

But two things always demand attention - the desire and need to move from active to passive attention, and the need to move defensively in late markets and late investing careers.Defensive investing is a way of separating your cash from debt in a mature market to mitigate the impact of any kind of correction. 

A lot of the location question comes down to your goals though as many folks are taking pretty slim cash flow so they can live in desirable areas.