Since I live South of Boston, I'm not real savvy on what's shaking in Southern NH (except that if my Wife decides to retire some day, So. NH is likely where I'll look to relocate).
Yes, Marblehead is a very nice/expensive area. Houses were typically $1Mill starting point a few years ago.
You probably want to stay away from actually working in the City of Boston proper anyway for the following reasons:
- City has "home rule" and makes up lots of rules on its own. Licensing fees to the city whereas no such exists anywhere else in the state, all sorts of restrictions, etc. [Can't speak to RE agent issues but as an example, I'm a Constable - in Boston I'd have to pay a $400 fee for my appointment and another $450/year for unspecified "training" plus more if I want to carry handcuffs, more to carry OC, more to carry a gun, etc. In the 'burbs, it cost me a single postage stamp to get appointed as a Constable!! I carry what I want to and need not pay homage to Mumbles Menino (Boston Mayor) or similar jokers.]
- City has its own anti-gun and anti-knife laws. NO ARs by city residents unless possessed and specially licensed back in 1988 (IIRC), similar bans on hi-cap rifle mags and probably more. Those of us who don't live in the City don't need to worry about it, so we don't.
- Parts of the city are shooting galleries (both guns and drugs). The police stay away from those areas except for sweeping up the trash. You don't want to be showing properties or even seen in those areas.