having owned a 95... im a convert.
the electronic controls offered 2002 on are nothing to fear, and work great when your not locked up. wish i had em for icy snowy roads.
with the way the prices have dropped on the early 2002's on, theres no reason to invest in less technology, unless of course you WANT an older truck feel. that i comprehend. and frankly, you'll still get it with a newer one... this IS a live axle truck, and you will know it on crappy roads. dont expect IFS feel. i dont live wheres theres smooth tar, so i get to feel the difference every day.
make sure you get the dealer maint records and see whats been replaced. you'll find some doo dads quite spendy if they break on you.
i do wish i had the v8 and OD transmission, but if i was to "trade up" i wouldnt waste my time on a pre 2002. id get as new as i could afford, as they keep improving the truck.
big ticket items? prop shafts. name a shaft, its expensive. make sure they are in good order.
apparently window regulators. my back two clank... i live in fear. make sure you have recent ones, as, i guess they go.
check the lockers, by wheeling. mine "worked" when i got em, but i found on a hill they will fail if theres a vacuum leak or the booster pump goes. which i had. to top it off, the center is vacuum controled only and when it opens, the idiotic locker control board thinks you turned them off and it opens all the lockers. (im currently converting my system to a 461 style, since theres no advantage to that crap in my vintage).. vacuum pump. make sure it works.
you do not want a squeaky AC fan. it could be near death, is expensive, and is located close to china if you are digging into the dash.
ignition key steering/lock cylinder failure is an issue... make sure that feels right. i was lucky. mine froze off and i could extract everything and move the cylinder. others have dealt with worse.
i didnt have any rust issues so i cant tell you where to look there.
im sure theres more, its a used car. its as much the PO as anything, so good records are worth the price! happy shopping. dont rush in.