Well you just need to shovel the small areas, like the walks and steps. It's good exercise. There are tools to handle the larger areas. My snow thrower set me back about a boat buck. It's more than 15 years old and still running good (Tecumseh 8 HP Snow King Engine). As for the temps, not usually a problem if you dress for it.

I hear you though. These winters would be tough to put up with after living in San Diego, and New England isn't cheap either in the more desirable areas.

There are pros and cons to anything and any place. You just need to settle on the compromises. There are also different stages of retirement. There is active retirement, then there is a stage where chronic health care issues might require nearby facilities. Ultimately there is the possibility that assisted living might be required. If you have close family, the best place (at any stage) might be near them. I have a number of friends whose elderly parents "retired" to FL and ultimately moved back to New England to be near their children when they realized they needed more care.