I have a 97 Cherokee that we use as a weekend exploring rig and toad.
Paid $600 for it with a dead water pump, threw a new one in, replaced some broken interior parts, lifted it, new tires and all new cooling and suspension parts (tie rods, everything). In it for about $2k total.
Like you, it's a limited usage vehicle that we use as a convenience/entertainment device rather than depend on it. For that, it's perfect.
Cherokee, IMO, unless you're into some serious serious wheeling is a better pick than a similar year Wrangler, especially if you want an automatic:
1. MUCH cheaper. I have less in my whole rig than you could ever reasonably get a Wrangler for.
2. AW4 transmission > 42RE by a mile.
3. More room.
I wouldn't be too afraid of miles. The 4.0L I6 is a little archaic and lethargic, but it's dead-nuts reliable. The AW4 is a Toyota-sourced transmission that seems fairly un-killable as well. I've got 193k miles on mine, and wouldn't hesitate to take it anywhere.