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I would look for a vintage sled with boogie wheels in place of slides. The slides need snow to keep them cool, plus the older sleds are much lighter and cheaper. Also make sure the track is studded or you will want to stud it if on bare ice a lot.
A buddy and I burned up a 96 Polaris Indy 500 pulling my portable and gear it did last 2 seasons of fishing about 4 days aweek but it was rough going any kind of slush or deeper snow would put a stop to everything. You might be better off with a 4 wheeler if there is little snow you can stud those tires and not have a problem, even a honda big red 3 wheeler will do the job. Just stay away from "trail" sleds unless they are 2ups.
I would personally look for a utility type of sled or a touring sled.An older Tundra II would be good or even a yamaha bravo if you are not too heavy.These would also be the cheapest.As for bare ice You need to get some Ice scratchers. I hear good things about the Slidekicks brand as they are made so they don't get bent up when going in reverse if you forget to pick them up. They retail for about $60 for a set. I am considering these for my 2 sleds but usually don't have to worry about bare ice here in AK.I am a Skidoo guy myself. Have a 99 tundra II that is pretty much retired but still runs good an 08 Tundra 550F and just bought a 2011 Expedition sport 600ACE.I went with the newer sleds for comfort and suspension that the Tundra II is lacking.Just be sure to avoid any of the race style sleds those usually are marked with an X on the end of the name. they are definitely not designed for towing anything.
My icefishing machine is a 1972 ski doo elan 250 its all set up for fishing and towing my portable shack.. The best part about the machine is i can load it in my truck by myself super light.. Huge bonus when newer sleds have issues in early season slush... The shack sits across the custom seat i made during transport in my truck.. I have towed 2 portables with 3 people sitting on them and the sled didnt even notice..I will post some pics of this weapon soon
I would personally look for a utility type of sled or a touring sled.
Bart thought you just set a cat up for fishing. What the issue?