Any vehicle that is over 20 years old requires repairs and maintenance.
Are you capable of doing most of that yourself? If not, 20+ year old vehicles are very expensive to own.
I just bought my 99 Wrangler last month. I wanted a six cylinder, auto transmission, hardtop, AC, 2 door and the best condition I could find for the money.
I am happy with my purchase, I drove 400 miles to get it, although I have been doing numerous repairs since I bought it. Small stuff, but still stuff that needed to be done to make it safe and legal.