I try very very very hard not to get stuck. It vary rarely happens.
In the last year, this was my only stuck where my winch was required.
As far as gear? That is a long list and depends on the trip and how long I plan to stay. Right now in my jeep I carry the following all the time...without exception.
A Viair 450C onboard air system with a two gallon tank.(permanently mounted)
A full set of Metric and SAE wrenches.
A full socket set.
Various other tools.
An ARB Fridge.
A transmission funnel.
Spare driveshaft that works for both front and rear.
A set of inner and outer axleshafts for the front. Left and right side.
On the roof I have a Pelican gun case mounted permanently to the roof rack which holds...
Two tow straps.
One tree saver strap.
Winch controller
A case of electrical connectors and various parts to repair my OBA system
An extra two D rings
A snatch block
and a multi meter.
I keep a 5 gallon Jerry can and a high lift on the back bumper.
Then I have my trailer for camping trips where all of my various camp gear goes in, two more Jerry cans and my roof tent.
Im sure there are a few things I forgot that gets stuffed into this corner or that but for the most part, that is what I keep in the Jeep.