Price: $3,800

The second-generation Jeep Cherokee (known by fans by its internal XJ moniker) combines classic looks with rugged ability. The final 2001 model year also sneaks below our $5,000 price ceiling.

In its final years, the XJ Cherokee came with a 4.0-liter inline six producing 193 hp (144 kW). All of these Cherokees have four-wheel drive, but there are a variety of systems available. The standard Command Trac powers both axles, but this is only really possible on low-traction surfaces without harming the mechanical parts. The optional Selec-Trac version features a mode for full-time four-wheel driving that's fine to use in all conditions.

It's also worth noting that if you want an XJ Cherokee, you need to act fast because prices are on the rise. While there are still affordable examples out there, pristine vehicles can go for quite a premium. For example, a beautiful 1999 model auctioned for $21,699 on Bring a Trailer in June 2018.