Had a 2005 Laredo w/ the 3.7 and just traded in a 2008 Limited, loaded, w/ the 5.3. I've had a lot of Jeeps and am biased towards them, but my experience was less than stellar, but I would not run away from the right one at the right deal. There are better options though.
The '05 was pretty basic, but had transmission leaks and a few other, relatively minor drivetrain issues. Decent car, cloth seats were durable but stained really easily.
The '08 Limited was a bit disappointing. Decided I finally wanted a higher end daily driver and this was a decent car but it had some irritating and one dangerous issues.
The electric xfer case shift mechanism pulled the car into neutral on a few occasions, once after I shut the car off possibly when sitting w/ the key in finishing a 'phone call. Luckily I always set the handbrake, however my Wife and babysitter also drove it...this one got my attention. I heard clicking and an electric motor sound a few times when shutting down then one morning, I tried to drive away and the xfer case was in neutral w/ the Low Range indicator glowing slightly. Dealer got me in the next day when I called on this one.
HVAC resistors overheated at ~30k miles causing a noxious burnt electronics smell, fixed once and the smell started to return when I traded the car. The radio/nav/bluetooth was OK but would lose my phone every few months, had to completely reboot it once or twice. The vinyl portion of the "leather faced" seats cracked down to the fabric at~25k miles/3 years...unacceptable. I wanted to like the car, but it just wasn't up to its intended market. Honestly, this one sold me on a Range Rover. Figured if I was going to have reliability issues anyway, might as well get a Rover...
That being said, they are decent, safe (crash wise at least), easy to work on w/ good all weather/off road capability. I'd probably look elsewhere first, namely the Asian midsizes, but if you really want one of these, look for a base one.
