I am a current owner of an '04 Overland and a former owner of a '96 Limited V8 ZJ. Love and miss my ZJ, by the '04 Overland is better in every area. I sold the ZJ at 212K with no major issues. I bought this WJ at 93K and have had it for 4 months. Absolutely love it. It is a great continuation of the JGC line from the previous generation.
I had a 3" lift on the ZJ. No problems. Never got stuck in mild wheeling. I am planning a 3" lift for the WJ before snow (though it'll be a 2" lift from the UC suspension on it now).
My two cents here echoes what's already been said...as a daily driver, I would go with something newer rather than older, even if it means paying more. Since the TJ is paid for and you're not in a hurry, shop until you find the right one. I wouldn't waste time on Jeeps that need "just $100 fix at the dealer". If that's all it takes, then the seller would've fixed it. If they haven't, then what else have they neglected?
An Overland is special in many ways. It is still absolutely spotless, but wherever they had it serviced didn't know squat about an Overland. Wrong diff fluid and transfer case fluid.
Anyways, good luck. Upgrading you Jeep is fun. Upgrading from a couple to a family is infinitely more fun.