So I have a fixed I'm happy with, but will be moving to Breckenridge and don't really wanna deal with spinning down hills and dying going back up. So going to freewheel, lowering the GI to somewhere around 58, replacing the risers with road drops and putting brakes back on, and getting cross tires.

My question, mind I will be dealing with winter conditions often, is whether or not it is worth my money to get a cross fork with a cantilever up front or will I not really get that much better brake power on the rims compared to baseline Tektro calipers I already have? Would it be a smarter buy to just get nicer (roomier?) calipers? Or should I just stick with what I have cause upgrading wont really do enough to warrant the expense?

Get a SSCX bike and call it a day.

Leave it as is unless you want to go disc.

Cantis won't be noticeably better that calipers when your rims have a sheet of ice on them or are packed with snow.

Winter biking in Summit County - don't get run over by a gaper.

I could be misinformed here, so someone feel free to correct me, but my impression is that cantilevers don't provide added stopping power over standard calipers (I've actually been told its less), just increased clearance for wider tires. If you can fit the width you want in your frame without changing brakes, save your pennies.

Linear pull cantis? As mentioned, with ice covered pads and rims there won't be any noteable difference, but in normal conditions I feel linear pull cantis may provide better stopping power over standard cantis.

you're confusing a few issues. tire clearance is mostly dependent on your frame and fork. depending on the frame you have, if its a road or track frame will determine the maximum tire width, not the calipers. long reach calipers can be used to fit wider tires, but only if the frame accommodates them, and most road/track frames do not. canti brakes, in general provide less stopping power than good calipers, mini-v's are a better option if you need better stopping power and you can sacrifice some tire clearance, provided you have canti brake studs on the frame/fork. most road/track/fixed frames will NOT fit cross tires, unless its made for that purpose.

How about getting a Sturmey-Archer S3X hub?

I always thought that fixed was a little nicer than a freewheel for winter because you can slow down without braking. But it's been 30 years since I rode fixed, so this could be wrong

In my experience it applies. I did a ride last December on nice dry and clear roads, and then went on a trail that was covered in snow and ice. Felt pretty much in control, and there was noticeably less sliding. Sort of the same for rain.

If there is a Kilo of SSCX with disc this might be the answer.

I would generally stick with fixed, but I'll be in the mountains. So spinning in iffy conditions so that my GI isn't annoyingly high for the hills doesn't sound too fun.

That's how my winter bike is set up: