I've lived here all my life. I have been to other places on extended visits- not vacations- I have brother who travels the world and buys a house wherever he goes (buying a house to him is like me buying a pair of running shoes).
I have to say that I LOVE upstate NY. I understand all the problems people are mentioning. I enjoy the change in seasons- I've learned to enjoy any extreme in weather- it makes the perfect days that much better.
I live just south of the Finger Lakes and would move up there in a heartbeat if I could get a job up there- I'm happy where I am, though.
The small cities are kind of cool if you overlook the bad things. But, then NYS is a great city with a lot of horrible aspects.
As far as the weather, we rarely get the extremes like tornadoes, earthquakes, hurricanes.
Except for the recent flood, most weather issues are a day or two of inconvenience.
If you like the country, it's beautiful. It's very safe where I live- women don't hesitate to go out running, at night, alone.
I would say that the quality of life if you have a family and a decent job (like I do) are great.
Ithaca is an awesome college town, the surrounding areas are beautiful.
The Catskills and Adirondacks are awesome.