What do I need to start? overland?

A 3 piece bed platform has worked well for my wife and I. We use a 4" trifold mattress on top of our platform and this lets us carry whatever we need to in the back like tall coolers, mountain bikes etc.
It's far cheaper than a RTT or decked system and doesn't require any tools to install or remove. It's not hard to make yourself since it's just 3 boards that are 24"x 56.75" and the notch for the tailgate area. I've also made a 6' model for a 5' bed (with the tailgate down of course) If you'd like more advice on how to DIY this, let me know. Material cost is about $300 these days.

 

Start with the "Ten Essentials", some half decent camping gear and go hit some easy trails. If you want to push it harder and get out there further, then start thinking about all the expensive goodies.

 

This will answer all your questions on how to go Overlanding in a Toyota: https://youtu.be/HM2TdWQg2BQ?si=sCASCvEmmCadUP6r

 

Joolca Hot water Systems are awesome.

 

Honestly. You don't really need a RTT. You could just get a really nice ground tent. But, I will say that RTT do make camping convenient and comfortable. The older I get the more I lean hard towards comfort and convenience.

 

I can totally relate. I tried all sorts of sleep systems and end up just leaning the driver seat as far back as I can get it and sleep. This way I don't struggle to get up in the morning. I just open the door and slide outt

The days where I can sleep on the ground in a sleeping bag are long gone(ha ha)

 

Whenever I see a decked out overlanding rig I think how ridiculous it looks and how they spent way too much money to go camping. Weight is the enemy of offroading, so my advice is to skip steel bumpers, body armor, and winches, unless you plan to get really radical. I used to work for the Forest Service and have seen too many situations where a winch is useless without another vehicle to attach to. In the forest this is fine, but out in the desert a winch without a companion vehicle is completely useless. In my experience, the #1 thing to help me in driving off-pavement is airing down my tires.

Seems like I'm just repeating what other people here have said, but here we go. For recovery gear, I use a second jack (I like the bottle jacks), I have RV jack stands to set my jack on, a flat tire kit, a pair of traction boards, a good shovel, and an air compressor so I can air down my tires. I also throw in gloves, a small tarp, some clean rags, and basic tools. I put all this in a plastic storage tub so I know where everything is if I ever need it.

It looks like you already have larger tires, so I would add a truck topper with a sleeping setup for yourself. And no rtt! Why add 100+ pounds to the roof of your vehicle? Get a topper and keep everything inside. If you like the overlanding look, there are some less expensive alternatives for toppers.
https://overlandvehiclesystems.com/Expedition---Truck-Cap-W/Full-Wing-Doors

After that, I'd save my money for gas, firewood, and really cool camp chairs. I use a ground tent, but have a nice thick air mattress. My friend, for comparison, sleeps on a cot under the stars.

Just got back from a back-country camping trip in Death Valley with the family. I got off the beaten track of popular backcountry roads, and I even got to put it in 4wd in a few spots. I have a topper on the back of my truck and shoved it full to the gills with camping gear, water, food, and firewood. The most useful thing for me besides the truck shell was the windoors that allowed me to access the front of my truck bed.

It was an amazing trip and my truck is mostly stock and I have nothing that would be classified as overlanding gear. I just use it as an example to show that you don't need expensive overlanding gear and you don't need to beef up your truck with thousands and thousands of dollars of mods.

The two most important things I can't stress enough is that you don't need to spend a ton of money to go camping in the backcountry and to just get out there and have fun.

 

Overlanding can mean so many different things to so many different people.
There is a large group of people that send a lot of money simply to camp a couple weekends a year sometime in well manicured grass lawns.
Our family is not in that group. We are constantly outdoors, camping, riding, hunting, hiking, etc. Overlanding makes sense to us because we like to camp outside of campgrounds, down gnarly roads, secluded away from people. I never understood why people left the big cities to camp in a tent in a crowded campground. Seems counterintuitive.

We are an average middle class family and built our overland vehicle on a budget.
First major modification was a good suspension.
Second a used roof top tent off marketplace (Ill expand more on this)
Third we built our own drawer system complete with refrigerator draw slide drop down(took me a couple iterations to get this correct).
We then added a front bumper with winch since we often snow wheel and adventure alone. (No need getting the family stuck and having to call a tow truck, we have trees here so I can use the winch).
Next an awning for summer sun and rain showers.

We have added many more things and will continue to do so. Its an ever evolving thing, my best advice is to get out and spend a couple nights in the woods with what you got then start upgrading if needed.

Back to the roof top tent. I was originally sold on its "convenience" soft top RTT are anything but convenient. They are heavy and a pain in the butt to put away especially when you add an awning. They are however very comfortable and cool. I know Ill get some flak for that but sometimes its nice to be comfy and fun to look cool. We even got the annex. If you aren't moving from spot to spot the camp setup is rather nice.
We live in the suburbs but park in the garage so after each trip we have to remove the tent from the truck and store it. Another inconvenience to keep in mind.