I'm not sure about Windsor, but around Ft. Collins and Loveland rent is about $1000/month for a decent 3 bedroom house. There are many between $1000-$1500 available. At those prices you're pretty much better off buying. Before we bought our house last summer, I was paying $700 for a duplex in Loveland.
Windsor is really booming right now, both commercially and residentially. A couple of guys at work live there, they really like it. Our managers wife has a manufacturing business on the north side of town, they make jeep tops for bestop. I wouldn't want to reccomend any of my friends to go work there though, it's kind of a sweatshop

.
As far as TDR events, I think we have a good group here, those Wyoming guy's don't ever do anything on the good side of the border, or at least they don't tell us about it and keep it all to themselves

. But, yeah, we have some cool events, dyno days mostly, the occasional wrench day, we are lacking in the beer and BS'ing department though. Kudo's to Tim for doing his best to fix that.
The weather is relative. I don't know how else to put it, it seems pretty mild, but my mild might not match your mild. Usually, when it snows the roads are clear by that evening, but lately our last few storms have made the snow packed roads hang around for a few days at least. Really not to bad here, as long as you like city stuff, you'll be content. I am going to move back home (Wyoming) after I've taken my piece of this economy, I just don't like big cities much

(50,000- 100,000 is huge to me).
Anyways, good luck with your decision, if you have any questions feel free to ask. If you decide to move on out, make sure you let us know.
Matt