At some point you just have to stop taking more gear in my opinion. Take a smart amount of gear, but don't go overload
A minimal kit and a good head on your shoulders will get you out of a LOT of bad spots.
-Tow strap, generally a long one that can be doubled over to make a short one to multiple attachment points. One time I had to use a long tow strap and a big stick to form a pulling device. I basically hooked the strap up to a tree and the vehicle. Took a big thick tree branch and made a lever with one end in a loop in the middle of the tow strap. Then you just twist the stick round and round causing the strap to get shorter. Amazingly it worked. I originally saw it in a movie when I was a kit....blue truck, water crossing, maybe in Australia? ( have never been able to find the movie ). You can also use a tow strap to tie a vehicle off in a scary predicament. Nothing like having your vehicle over the side of the road with 100+ feet still left to go to the bottom. In a pinch it can also be used as a tree strap, used to pull a rock or tree off the road, etc. Is it ideal for those uses...nope....will it work....yup.
-D-ring, preferably two. If you have to you can usually rig up an attachment point on one vehicle and not the other. I have seen a tow strap used with the strap fed back through the loop to form a noose at both ends. If you loop the noose over the tire you can sometimes get it very close to where the axle tube attaches to the springs. Not ideal AT ALL, but it can work in a pinch.
-Shovel. I don't generally care what kind. ANYTHING works better than having to take the license plate off and use that. There will be times that you just can't get the shovel under the vehicle like I mentioned before. Generally I like a full size shovel with a full length handle if you have the room, if not a D-handle shovel isn't bad. Spend some time with a file and your shovel. Coming from a 10 year background in Wildland fire....a sharp shovel is a happy shovel and operator. Careful when using a shovel under a vehicle. You can get it caught on brake lines, wires, fuel lines, etc. That sucks, ask me how I know.
-Axe. There is a whole thread on how much you don't need an axe, but when it comes down to it, an axe is a FANTASTIC tool. It's not so much about just chopping things in half, but also about what you can make with one if you have to. It also can function as a decent hammer if needed...not recommended however since it ovals the eye out.
-Bottle Jack. It is very handy if it starts really short and gets really tall. Some fords and land rovers had factory two stage bottle jacks. They are not that expensive anyways. I don't generally buy into the hi-lift jack thing. They work great sometimes but generally I can't justify the size and weight. Most new vehicles don't have very good attachment points for a high lift either. A jack also has a lot of alternative uses....you can use it as a press, to help remove tire beads, etc. Having some cribbing around can be a good thing, but I generally don't want to take up what cargo space I do have with wood. Get a better bottle jack and most times you don't need cribbing. If you happen to need some, it can be made with the axe
Those 5 things have probably gotten me out of more bad situations over the years than anything else. By all means if you have the means get a winch, any winch. It doesn't have to be the newest wiz bang fancy $5000 twin motor gigglepin wide drum model. I have a $175 used Belleview upright winch on my willys. FANTASTIC winch, especially at a price like that. Some other things I have found VERY handy over the years....
-Jack base. A piece of 3/4" plywood works great. I have always liked a round piece that fit in the spare tire and wheel. Get creative and see what you can come up with for an interesting space saving shape hidden in an different area.
-Bow saw. A saw is nice to have. It can be better in certain situations than an axe, but I will always pack an axe first. You can make a nice 24" blade, 8" dia cut, collapsible bow saw for about $10-15 with a trip to the hardware store. It breaks down and stores in the handles, about 1lb or less, easy to store.
-Tools. I think this is a separate category. Breaking down vs getting stuck. I have used a lot of tools to help with recovery though. Don't go overboard however. Your vehicle will be a lot happier without an extra 200lbs in tools constantly in the back. Build a decent kit that will fit in a soft tool bag, have it be able to be strapped down in its home, and don't use super high quality tools that you can't afford to loose or use to help weld an axle tube back together on the trail.
-air compressor. Airing down is probably the most beneficial thing you can do for vehicle performance. Most people don't air down enough because they are afraid they are going to loose a bead. An air compressor helps ease these fears a little bit. Learn how to air down properly and deal with odd tire issues like loosing a bead.
Get out, get stuck, get yourself out, repeat....
