I have lived in Maine virtually all my life and my history goes back to the colonial period in Maine on my mother's side.
I have been to Portland MANY times. The city and its surrounding area are great. It is sometimes called "Little Boston." It is a very progressive small city with wonderful quaint historic districts. The premier district for restaurants, shopping, and night life is the Old Port area. It is a safe city. While I am not gay, from what I know it has a significant population though nearby Ogunquit and the area around it is especially known for this. Portland and southern Maine especially, again, are very progressive and welcoming, as is the state in general. You know of course that Maine just made history with its affirmative people's referendum on legalizing same sex marriage.
Occasionally my family and I go to Portland for an overnight to take in a show and enjoy the city. We've been there for concerts and musicals. Yes, Maine winters are cold and pretty long but I know from experience it gets plenty cold in Kansas too (was there when in the service). In the summer Maine is especially wonderful with the beaches up and down the coast, Acadia National Park, Baxter State Park, etc. We have the BEST outdoor rec ANYWHERE. In the winter, skiing is huge if you are into that with places like Sugarloaf and Sunday River. In Portland you are close to New Hampshire and Boston. You can take the Downeaster Amtrak to Boston at great prices.
The University of Southern Maine with its law school is right there and is a good college and law school, all part of the University of Maine system. There are other colleges in the region as well.
Maine is considered to have one of the best qualities of life of ANY state, if not THE best according to many recent publications.
My family and I love it here. Happy Holidays, and let me know if you have further questions.