Ken - Move SOUTH of Boston, the weather is better with less cold and less snow (of course, unless your job is north of Boston) and the good fishing season can be as much as a month longer (it's almost 2 months longer in Rhode Island than in northern Mass/southern NH...
Ten years ago I had an 19' SeaRay that I had slipped in Quincy. It was a little too small for the harbor - I would highly recommend starting at 20' and moving up from there.
Personally, I now live in Rhody but work downtown Boston - commute is 90 minutes plus each way and it got old after the first week and near miserable since. But the housing prices are incredible when compared to those around Boston. The typical 3-4 bedroom house in my mother's neighborhood in Dedham (just sw of Boston) are fetching high 400K - low 500K. The same house in OK areas of Rhode Island is almost HALF of that and in some cases less than half...
The problem with the ramps goes away with the best fishing, which is first light. The worst of the boaters typically don't come out until 11am so you are just dealing with that when you haul. Evenings into night are also excellent fishing and most of the yahoos are off the water then. One thing to consider is that there is little ramp access immediately around Boston. It gets better north and south of the city. Here is a link to the states public ramps:
http://www.state.ma.us/dfwele/pab/pab_toc.htm#PABsites
Never fished west/central FLA but I've had more than a few Rum drinks down there in my "youth"
