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.
body88, I spent 41 of my 44 years in Boston. I know exactly what Boston (New England) weather is like and the summers are getting shorter and shorter while the winter (cold months) are getting longer. Boston still has occasional snow in March and April (I remember specifically getting 3 feet of snow on my daughters birthday in April). When I said fall lasts a week I was referring to the change in leaves colors. You blink, you miss it and don't tell me differently as I stated...I lived there. The 90 degree weather you are referring to comes as a heat wave and lasts maybe a week. Air is so thick you could cut it with a knife. The cold comes in mid September and by Halloween you have to bundle the kids in parkas so they don't freeze while trick or treating. I don't hate Boston (New England) and its nice to see changing seasons, but I'm done living 75% of my life in temperatures under 60 degrees.
As far as the pay, that would depend on what you are doing. I make far more per year than I did up there...which I thought was weird too, but like I said...it depends on your job. Even my sister who is a medical assistant and phlebotomist would make 2x more money here than in there.
You stated Florida is "backwoods" but the majority of people I have met down here...are from the North East...Boston, New York, New Jersey, etc.

As far as the cleanliness. LMAO I started to say maybe Boston's focal point of places such as Government Center, Haymarket Square, etc would be kept clean...but then took it back because to me...they have always had trash and whatnot spew around. Back Bay is nice at times, but has it's moments as well. Let's talk about the neighboring towns such as Somerville, Chelsea, Charlestown, Roxbury, Mattapan, Lawrence, Dorchester, Revere, Lynn, Malden, Everett, ... cripes I could go on. Granted I don't live near near Florida's capital (Tallahassee) but the only place I have been told is a place you don't drive through due to "safety" considered "ghetto" is Belle Glades (and I'm sure some parts of Miami). Historically, yes it has beautiful architectural buildings...Florida's tropical buildings are beautiful as well. The pink, salmon, beige, cream colored stucco and clay roofs look amazing from the sky. Everything looks alive when flying into PBIA...while I cannot say the same about flying into Logan. Even the water looks different.
Everyone's opinion is obviously different. But having actually lived in both places, my opinion is that Florida is (for me) the best place to live.