Couple things. First, I had the pleasure of my first powder tow out a few weeks ago. Always did the ski loop to bumper tow......on/near packed snow. It doesn't work in deep snow IMO. With a rider ont eh dead sled, it was too heavy to get enough speed to pull any sort of hill. WIth no rider on the dead sled, it would NOT stay upright. I could get a good head of steam going then first couple turns, it would go upside down real quick.
What ended up working was 2 tow sleds, long ropes, 20'+ tied to the bumper or suspension of the dead sled and a rider on the dead sled.
For the guy with a trashed track/skid.
1. Rem the whole track/skid, flip the skis, tow it out backwards lashed tight to the pull sled.
2. OR get one of those plastic sheet buddy tows and pull it forwards with one or 2 pull sleds.
3. Haul a new track and skid out there and replace it if the tunnel/driveshaft/case is ok. Propane torch or 2 is real handy and maybe do a mock replacement on a similar sled in the garage before going if unfamiliar with replacing a track.
4. Is it possible to wire the track together with some heavy tie wire just to get it to somewhere you can tow it or fix it right?