I've owned 5 all together. The last 2 have been toads. The previous was a 01' Sport. I have always owned manuals. I think it gives you a much wider power band and overall more fun to drive, but that is my .02 cents.
Some things to look for? Here are some suggestions. The lower the miles the better. Get on your knees and look under the chassis. Look for frame scrapes or damage. It will give you a clue as to how it was treated. If it in an older Jeep, check the back of the valve cover for leaks. Some years had habitual leaks back there. Go to www.jeepforum.com
and do some reading. You will get a real flavor for the the different models and their reliability.
Don't buy one that has been excessively modified unless you are really good at troubleshooting mechanical issues. Sometimes owners build in one problem on top of another with their modifications.
All in all I think the Wranger is the perfect Toad. We love it and it gives us another dimension in our travels. We love to go off road exploring and seeing things that you can't see from the road.
Good luck, there are tons of them out there.