Re: Where to live?
I grew up in OOB, (as Old Orchard Beach is called), it is a small town in the winter, but please be aware that in the summer it becomes a tourist town. The population BOOMS, lots of Canadian tourists and out of staters. Depending on where you live, you could have all night party neighbors, so you want to make sure you don't rent or buy in the downtown area. It has, like all other towns, nice neighborhoods, but also very cheesy areas. One of the nice things is the beach, you are less than 10 minutes away no matter where you live in OOB. 7 miles of beach is nothing to sneeze at. If you are looking to buy a home, taxes are high in OOB. As far as commuting to Portland, it isn't far, 20-30 minutes depending on traffic. Scarborough is generally a nicer area, and Saco is great too, of course, the rents probably reflect this. I probably wouldnt live in Westbrook, it is a mill town, but I am sure there are nice areas there too. Biddeford is kind of the same, there are some really nice areas, but Main street is awful, and there is actually a trash facility in the center of town.

Taxes are better, and the commute is easy. Rentals and prices of houses are better in Biddeford, and there are some really nice areas.
As far as winters go, you can never tell. This has been an easy winter as far as snow goes, but it goes from 27 degrees one day to 62 the next. Theres and old saying in Maine, "if you dont like the weather, just wait a minute", and it is completely true. I wouldnt be to concerned about traveling and snow, we all adapt, and if it is too bad, school is called off.
If you have four wheel drive you are all set, or just get snow tires for the winter. Good luck, and if you have any questions feel free to email me!