The 2nd gen's handle a little better due to better sway bars mostly, and you can upgrade any of them. If you need a serious rock crawler or off road rig, the 2nd gen's take more work to be competent, but IMO they are better on road.
The 302 and 4R trans are very reliable but at this age most people are neglecting things. The water pump is a PITA to do on any 20+ year old SBF, the timing cover too. Besides basic known items like those, you should love any 98-01(I prefer the upgrades done on them compared to the 95-97's).
If you hunt one, notice the slight changes to body trim items. The wide fender flares came on many Explorers, none on the Mountaineers, in 95-98 they were rounded, and 99-01 they had a sharper outer edge. It's a taste thing, see what's out there and narrow your search.