Well, I actually just put some money down on a used 870 Wingmaster ($150- wow!). Was kind of feeling like I jumped the gun, even though I waited, b/c it's not capable with it's barrel of getting a choke. But... thanks everyone for making me feel better about this purchase!

I can vouch for the 10/22 as well. Only had mine a year, but I (and more importantly, my gf) love it. Fun, cheap to shoot, tons of after-market goodies, and pretty rugged.

As for my rifles, I have a few WW2-vintage things. Fun to shoot, maybe to hunt with. So... being you're in Canada (IIRC), I'd maybe peruse some of the weapons made by countries similar in latitude. Russian guns, Swedish, etc. Probably not as "sexy" as Winchester, Remington... but probably better suited to your environment.

For example, if I were a hunter, I'd probably take my Russian M44. Short carbine, big round (cheap if surplus), bolt action that holds 5 rounds, and easy to operate with gloves. I'd probably buy a new stock for it though, as the standard issue is pretty much a straight stick.

Best advice though, is shoot before you buy, and research the options for what your intended purpose is. Fun at the range would be the 10/22. Home defense, a shotgun. Long distance hunting(ie, 100+ yards), a large caliber centerfire. Concealed through a rough neighborhood would be a pistol of some variety.