Here's my take.
Cherokees are cheap to buy and the drivetrain is strong on the 91's and up, but everything else on it will fall apart. - I own one and don't recommend it.
Toyota pickup or 4runners are very reliable but expensive to purchase and hold their value. Watch out for timing chain, headgasket, and frame rust issues. If I had 5-8 grand to spend this is what I'd get.
Suzuki Samurai - uncomfortable, loud, overpriced, but easy to work on and incredible offroad stock. - not recommended unless you're an offroader (I own one)
Suzuki Sidekick - inexpensive to purchase , easy to repair (unless the computer goes), suprisingly good offroad, pretty good fuel economy, and alot more suitable than a samurai for a daily driver. The downside is you'll look like a chick driving one.
If you're looking for an inexpensive daily driver I'd search for a good sidekick or Toyota Pickup/4runner.