For me...South Florida. Weather is beautiful 99% of the time. I wouldn't move back to Boston as it's just to dark and dreary for my liking. Winters suck, long, cold, dark and wet. The summer has shortened to about two months time with the added Spring teaser. Although watching the leaves turn in the fall was nice, it happened within a weeks time and was over and then usually dropped to 30 degrees, add snow (pretty first time around), then all the sanding, the city becomes very dirty. Down here in SF there is always color. Flowers are always in bloom. The ocean is clear and warm. It's sooooooooooooo much cleaner here all around. The people are friendlier and not always in an unrealistic hurry (although there are times that Floridians are too laxidaisy and slow 
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I love it here. 
Few points: I wouldn't consider Boston dark ( compared to a city like Seattle)..... The summer is defiantly longer than two months ( it gets warm in May, and typically you are still getting 80 degree days in early september.) It's 90 currently, and we where getting 80 degree days in late April this year. I agree that the winter sucks, but that is true of any city that has a real winter. If you enjoy winter sports, and a white Christmas, it's a big plus in my opinion. Also, spring and fall are extremely beautiful here, and they last a lot longer than a week. I wouldn't argue that Florida is not beautiful, but the constant humidity, and horrible mosquito's wear on you in day to day life. Also, the housing market and economy is pretty bad in Florida right now. You make less money down south, and there is a very large "backwoods" population in Florida. From a career standpoint, a city like Boston has a lot more to offer than most city's in America. As far as the sanding goes, I wouldn't say the city gets "dirty", infact Boston is one of the cleanest city's in America. The "sand" from the winter is cleaned by the city as soon as winter ends, there is a large budget for it actually. Not sure if you ever saw Boston ranked as one of the cleanest city's in America, but having spent time in most major Florida city's, I can say for a fact that Florida is not cleaner than Boston (from a garbage / bum)standpoint - I would say the opposite. There is no bad part of Metro Boston, as the "ghettos" are located outside the major metro areas. Boston is one of the most beautiful and historic city's in America, and although it is not tropical, there is not a city in Florida that is more beautiful architecturally than Boston - IMO. In the summer, Cape Cod beaches rival any beach on earth.
If you are the type of person that like constant humid heat, then of course you are not going to like Boston. But if you like a full blend of seasons, Boston is a great choice.
