Little late getting in on the discussion, but I moved to Rutland 2 years ago from Western New York.
This is my personal opinion, and consider that I really don't think I could take living in Burlington and dealing with the ultra-crunchy granolas day in day out...
Rutland has it's shitty parts (Wal-Mart plaza and area behind), and then it's nicer features. Social opportunities in Rutland itself are limited. but during the winter, Killington has a lot going on (if you can deal with expensive drinks and Jersey-Joey) during the winter.
Outdoors-wise, the Rutland region has a lot going for it.
Obviously you have skiing with Killington, Pico, and Okemo all within 40 minutes radius. Magic Mountain offers a great altenative to the big resorts and is a great place to go on a powder day and is about 45 minutes away.
In the summer, there is tons to do also. Awesome cross-country mountain biking right in town at Pine Hill Park and decent downhill at Killington. Great trail network in Pittsfield is within 30 minutes as well. Bunch of swimming holes and lakes to chill at.
I'd say that you would need to choose your priorities. If a thriving social scene is important to you, then Rutland is definitely not for you. If you don't go out much, and enjoy the access to the outdoors, then Rutland is not all that bad.