Tom, my background is in the LAMP stack, so mostly web stuff. I believe MSFT is still C/C#/Visual C etc, so I'm not sure if they'd be able to accept my resume (stellar though as it is )
Kyle, thanks for the super description of Indy. My wife really liked what you had to say.
I personally am a fan of mountains and outdoors-y things, so Ft Collins sounds fun. Plus NORAD! However... Those fires looked pretty scary this year.
Also Asheville sounds nice... We have a coffee table book of American landmarks, and the Blue Ridge Mountains are in there, really breathtaking stuff. Plus I'd have an "easy" time of doing the Appalachian trail later when the boys are bigger.
I live in the Raleigh/Durham area of North Carolina. We used to live in Durham (which we loved) but recently moved to Cary (sorta between Raleigh and Durham). Durham is a great town, but does have some bad parts to it (you will read about those if you do much searching). But we never had any issue and really loved it there - great baseball, great restaurants, great breweries.
In general, we're about 3.5 hours from Asheville, but we're also only 2 hours from the beach! Raleigh is a fairly good sized city but we're also only 4.5 hrs from Washington DC and about the same to Atlanta.
I also do web-based software engineering. Because of the Research Triangle Park here, we have a TON of tech companies. IBM, Cisco to name a couple big ones, but there are so many smaller-ish web companies here. Dice.com currently shows 1061 job listings for the Raleigh area. http://www.rtp.org/about-rtp/rtp-companies
We also have a lot of universities (Duke, UNC Chapel Hill, NC State to name just the largest ones). http://www.researchtriangle.org/assets/education/universities-colleges
The housing market here is strong and has been pretty strong throughout the slump the rest of the nation has felt.
For outdoorsy stuff, I traded rock-climbing for kayaking when we moved here from Tennessee. Lots of rivers and lakes for kayaking. Also a good bit of hiking - though mostly flat terrain. If you want mountains and a more "outdoorsy" vibe from the town/city in general, Asheville is the way to go. I just don't know what you would find in terms of a job there.
For Craft Beer, we have somewhere in the neighborhood of 20 production breweries within 25 miles and many many more that are just in NC (70 I think now!).
Let me know if I can help you with any specific info about the area.
Raleigh/Durham (Cary, Wake Forest and Garner are in surrounding area)