(3) The fact that most tax advisors, CPAs, retirement planners, etc. recommend something in no way leads me to believe that the thing recommended is the best move.  

That said-A CPA/tax preparer with real estate experience can help with the book keeping and taxes preparation - consult one on the front end of the process to know what records you need to keep.A fiduciary financial planner is worth a consult to understand and plan for how best to move your money out of your stock options.I'm in a similar situation and here are my observations: your stock options, RSUs and PSUs are all treated as regular income.

Look at www.MBTA.com and use their trip planner to see what options are available.Prices here are quite a bit lower than inside RT 128. 

@Jessica Jay-Maleski I was a City Planner for the Town of Gilbert for 5 years.

We have urban planners on staff to keep costs economical.

Your Financial planner should give you and connect you with right individuals. 

these things cant be answered on an online forum.easiest way to do this is simply go to the planning department and talk to a planner they will usually know the utls situation.

In my years of experience being a public and private sector City Planner, cities usually do not look to rid themselves of a MHP.

When that wasn't approved one of the planners advised that I either apply for rezoning to R-6CD (conditional use)  which would allow the current number of units and should be a little easier to obtain. 

If you have not closed, please check with city planner and building department to see if that was legal nonconforming or illegal.