It really does suck. Let's face it, the only people who enjoy winter in New England are those invested in weather or those who like to ski or snowboard. Outside of this, winter is generally depressing with the short days and dark by 4:30. It then takes forever to enter a weather pattern where we're consistently warm and not have to worry about whether outdoor activities will be ruined (minus thunderstorm chances).
With both my parents gone and the ability now to work remotely, I am strongly considering at some point re-locating down South. I still have family up here but my girlfriend's family and parents are mostly in Florida. I can always come up this way to visit.
I've even considered something like living in Florida from March - May and then September-November and then here from June-August. Just thoughts though...not sure if they will ever become serious enough to act upon but it seems like seasonal depression gets worse every year.