This is a tip my friend had told me about and I havn't tried it out yet. You secure the front of one sled to the tail of the other so there is no slack in either direction, forward or back. By using both sleds, one pushing the front sled and the other pulling the back sled at the same time you are able to get much higher. You might try this if it is too deep or steep for just one sled....
That would make sense. I know from experience that if you have several Jeeps/Toyotas/Samurais or whatever 4x4 you run, and you all have tow bars on them, and you hook the tow bars to the hitch of the guy in front of you, there is (nearly) no mud hole you can't go through! It looks like a big caterpiller when you get four or five of them all hooked together. (Oh yeah, don't be the one in rear!)
We use the "short strap" method to tow a broken sled out. Take a short piece of mule tape, (or rope, tie down, whatever), and tie one ski from the broken sled tight to the grab bar of the towing machine, with NO slack.
Personally, I use just about everything mentioned so far except road flairs. I used to carry them, but they always seemed to fall apart. I carry three completely unrelated means to start a fire; #1 a small magnesium/flint/steel fire starter, and a chunk of old growth yellow fir about 2"X6". #2 four tampons (for gas and oil) and waterproof matches, #3 lighter and cotton balls saturated in Vaseline wrapped in aluminum foil, they all work.
I also have a para-tarp in my pack. It weighs next to nothing and doesn't take up any room to speak of. I also carry some twine with me. It's actually #60 gangion twine. I used to longline/crab up north and out west. I still have a net needle full of gangion material in every rig I own. Old habits die hard. All I know is it is strong and doesn't weigh much and is worth carrying.
I've made some good repairs with wire ties and mending twine. (Several trailing arms, one A-arm and one broken track).
In my opinion, the BEST way to learn what works for you, and what doesn't is to TRY it! Spend a night or two out there each year with what you normally bring with you. Even if you spend it next to the trail or even within walking distance of your rig. Try it all out, you may learn somthing. You do NOT want to be unprepared when it counts. We used to do it a couple times each winter when the kids were younger.
I think I'm going to try the track-winch thing next time I go out. I've been using a ratching tie-down for a mini "come-a-long" for years. This might be easier. (Not to mention a LOT faster). Thanks for that one!