In 2008 I purchased my first Jeep (used), an Overland '04 with 28,000 miles. I can't say enough about this vehicle! I love it! It came with everything except the engine heater. It now has 51,000 and it developed a timed squeak from behind the glove box. That's it.
My '04 Overland is my 3rd Jeep and I still have #2, a '93 Cherokee Sport with a 5 sp transmission. I tow my 25' sailboat to various places on the Great Lakes with both Jeeps without a worry, usually 3-5 hour drives. 90,000 miles on both of them, and NO ISSUES worthy of mention!
They're not the most economical for fuel consumption, but the trade-offs are well worth it.
I can't imagine myself ever switching to something else. Certainly won't be a Toyota or Honda.
I recently purchased a 2004 Jeep Grand Cherokee Overland as my first car (I'm 17). All I can say is I love it!!! My parents have had 3 Grand Cherokee's (93, 97, 01) over the years all with the 4.0L I6. That is one hell of an engine, practically bullet-proof. All lasted with well over 100K on the clock, and the only major trouble was a rear axle seal in the 97.
Since I grew up on Jeeps, it was only fair for me to get a Jeep as my first car. The 4.0's were pretty slow, so I opted for the 4.7L HO V8, and man this engine is awesome. The torque is amazing, and the little Honda's and Toyota's are left at the line with their jaws dropped.
I take care of the truck very well (oil change every 3000 miles, rotate tires, check fluids, etc). I can honestly say this is one hell of a truck. I will keep it until it dies.
The Overland package is great; style, power, comfort, power, reliability, did I mention power?
I'm a true Jeep guy by all means, and they are the only SUV I will buy. Great truck with no rattles or squeaks, and only minor peeling on the chrome clad wheels at 80,000 miles. Talk about quality!