I've owned a TJ for the last 15 years. I have a 2005 6 speed right now. My best advice would be pretty much what everyone else here has said. Looks like you already have a winch. That would have been my first suggestion for a mod, but since you already have one I say, take the Jeep out get it stuck, use the winch and find out what you need to do to the Jeep to run the trails you'd like to run without getting stuck. My other suggestion is to use this community for any questions you may have. Most times if you have a question or issue the odds are there's already a whole thread here addressing it, but if you don't see one that helps you post up a new thread. People on this forum are very knowledgeable, and they love to share their knowledge with fellow TJ owners, so when you post you question you will shortly have many replies that should help you. I hope you enjoy your Jeep and being a part of this crazy community.... Welcome to the family. Cool dog, by the way. I have found that if you take the back seat out and replace it with a dog bed that takes up the space left it works out nicely. My pups love it.
