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We're based in Portland. I would highly recommend it. It is no colder than the rest of New England, the downtown is very walkable, decent school system, prices sane and the job market is not half bad.
My Observations (there are others, but these I have personal experience with):
South Port: in South Portland under the bridge, has a small year-round community. We spent a year there (about $5500 for a full year with power/water for 40'). It's a reasonable walk or bike across the bridge to downtown Portland. Plenty of safe street parking near the marina as well. Service department is as good as any place. The down sides are it is at the back of the harbor - about 2 miles to good sailing winds. Also some mud flat oders and bugs at low tide in the Summer.
DiMillo's: Awesome downtown Portland location. Secured parking lot that may be $50 or so a month extra. I think it costs a little more than South Port for the slip. They have a live-aboard community as well. Downside is the slips are tight - and I mean tight. Also probably 30 bars within stumbling distance is both good and bad...
Portland Yacht Services: Best service in town IMO. Facilities and location aren't as nice - though it's next door to Hamilton Marine. We're on the hard there now.
For a summer spot I'd recommend a mooring at Peaks Island (about $1000 for May-Sep - saves us about $2500 rent not being in a slip for the summer). No need to run the engine to head out and there's a ferry to downtown.
We're planning on launching this Spring to a mooring someplace in the harbor and then moving to DiMillo's for the Winter. I'd prefer South Port, but my daughter is in the Portland school system so we want to keep a Portland address.
We've been on the cusp of living aboard full time for a couple years now with plans to live and work in Portland. Stuff keeps happening like babies, illness and unfavorable housing markets. Although we're getting there and it looks like it will finally happen this Spring!
Let me know if I can help out any.
Martin
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