This is a loaded question...full of several other hidden loaded questions
Need more info.
1) How experienced are you with the whole "offroad" thing?
I dont ever recommend someone jump right into a lifte, locked, and loaded rig for their breaking-in period. I firmly believe that everyone who is learning to wheel needs to do it with a semi-stock vehicle. Inexperienced drivers put in compromising situations with Jeeps sporting 38" tires, lockers, and horsepower is a recipe for disaster, failure, and death. So where do you stand.
2) What is your level of mechanical know-how?
Jeeps range from almost 70 years old to present. Typically, the older the Jeep, the more you better know your way around a garage. Likewise, offroading takes it's toll also and can get very expensive if you have to take it to a shop everytime something breaks. This question is also a determining factor in buying newer (and possibly more reliable) or buying older and sometimes much cheaper...with the good possibility of having to do several hours of wrenching to get it trail/road worthy. So where do you stand.
3) What sort of offroading do you have in mind? (mud, rocks, trails, sand)
This is also going to determine what you are looking for in a Jeep. A mildly built Jeep can be fun in all these areas whereas a purpose-built Jeep is more one dimensional. A Jeep built for mud will not perform the same as a rock crawler, and vice versa. So where do you stand.
Lastly, you mention a $5000 cap. You can pick up a moderately built older Jeep for that or you can purchase a newer Wrangler in more stock condition and build it to your liking. Again, the above questions need to be answered first.
Talk to us and let us know what your plans/background are.