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Obviously more things go into a move than just what you listed there, but Portland fits your criteria (and the surrounding communities too). What are you looking at for a price range on a home? What type of business do you want to start? Are schools, services, anything else important?
1) Portland gets regular snow from December through March and you can get showers in November and April. Even a squall in mid-late October isn't out of the question if the conditions are right. It's not as much snow as Northern Maine, but I believe most would agree that it's more than enough.
2) Portland's the largest city in Maine with 63,000 people and 230,000 in the vicinity. There are about 450,000 people living in the area from Kittery to Brunswick. Portland is the state's hub of social activity, you won't find anything more active in Maine. It's a pretty laid back, relaxed kind of town with an easy-going social atmosphere.
3) Again, Portland (and just about all of Western Maine) is within driving distance to the ski areas and tourist destinations (is this important for your recreation or job prospectus... or both?). Portland is a destination in and of itself (the largest industry in the Portland area is tourism) and the surrounding coast is popular amongst tourists. Sunday River (Maine's largest ski area) is about 1- 1.5 Hours away from Portland and Sugarloaf USA is about 2.5 away. Tourists heading to both areas pass through Portland. In fact, Tourists heading to anything North or East of Portland (which constitutes the bulk of the state) will pass through Portland on either I-95 or I-295.... the state's only two interstates (yes, there's an I-195 and a I-395, but they're VERY short spurs, hardly interstates).
4) Once again, Portland's the best bet. It's thriving for such a small city (especially when you consider how small cities throughout the Northeast are struggling) and there's plenty to do when you consider the size of the town. It's the state's cultural and economic hub. Depending on what you want to do for a business Portland's probably the best bet (unless you want to run a hunting outfitter or rafting company or something along those lines).
Good luck!
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