...Don’t over think it. Drive what you have for a year, live with your gear for a year… make a list of pros and cons to all the gear you currently have along with all of your rigs strengths and weaknesses. After 1 year look at your lists and see what you really need and reevaluate before you start dumping money into this hobby.
I have to say this is the best advice. Most of my adventures until I hit 30 were 2 to 3 day hikes through the mountains, and it taught me to just keep it simple. When you start hauling around a lot of equipment, it pretty much destroys your experience, as you tend to focus too much on the equipment, and too little over where you are, and what you accomplished. On my hikes, I didn't even pack a tent, I packed a tarp, and rope. I saw so many fellow hikers pack their house with them, and they were just miserable the whole time, they couldn't see the adventure.
For me, since I am new to offroading, and my experience is more in backpacking, my loadup usually just consists of what a backpacker would take: food, water, and tools... like a poop shovel, a blade, and an axe. I do take a Harbor Freight 103pc tool set, and a Craftsman box set, but that is because I drive a vintage vehicle, that I am not afraid to scratch.
I have yet to purchase any 4wd recovery tools, so currently I stay off difficult trails, and only take routes I know I can take... there have been a few times I went places I shouldn't have though...