I've been interested in overloading for a few years now and I decided to start now. I recently purchased a 2015 Tacoma 4x4 and I'm from Central Florida. I am looking on where to start first on this journey.
Welcome!
My wife and I have a motto -- "Any Excuse Will Do". So as far as where to start....find an excuse and go!
Is there a brewery in the next state that you want to check out? See if you can find a way to it on as little pavement as possible. Maybe you've never been to a local watering hole or 4x4 trail, check that out too! And Overlanding -- while it's implied goal is remote, off-grid travel -- isn't always off pavement. Florida is full of interesting destinations that may involve more slab than track, but they are still worth checking out! Just pick a place you've never been before, load up the family, and go. The adventure is the reward.
You've got a great platform to work off of, but before spending a dime on it, use it and find out what you like, don't like, or would find more comfortable. The reason no two rigs are the same is that no two people have the same needs. Save your money (spend a few bucks on perhaps a Spot Device or an InReach, a shovel and first aid kit, and a map!) and have a great time. And most importantly -- take lots of pics, and share them with the rest of us!
Welcome aboard!