Not sure where you're from, but this isn't close to what I pay.
It depends on where you're going, but I've only paid a trail fee one time, and it was $6 for three days.  I already had an annual recreation pass that was $45 for the whole year, so I didn't pay that.
My insurance was $200 for the entire year. And it covered everything.  Oil is expensive ($48 a gallon around here) but that will last you like eight days out.
As for a ski rack, you can get creative and make your own.  Cheatah racks are tight, but expensive.  I used ratchet straps off of snowboard bindings and it help my skis tight to my tunnel/gascan rack with no problems.
And, it's worth it to buy a better/newer sled.  I had a 2001 Arctic Cat, mountain Cat 800 with a 144" track.  The engine/track length are fine, but all the weight is forward.  It really limits where you can go and how easy it is to double people.
I upgraded to a 2005 Ski-doo Summit, 800.  It made all the difference in the world in terms of the terrain I could access, and how easy it was to double people around.
I HIGHLY recommend getting good at doubling, and not towing.  towing is hard on your sled and limits where you can go.
If you have an specific questions, PM me.  and final word of advice... GET A HOTDOGGER.  burritos, hot dogs, anything wrapped in foil.  If you get one make sure to put it on a part of your can that does have the heatsheild.  Put it on the gnarliest, rustiest part.