go with a 2008, it will save you a load of cash. any way, it depends on what u will use the jeep for, not only what u like.
Grand Cherokee- good for hauling trailers, kids, an everyday vehicle. you can off road with them, but they are on the "luxury" end of the jeeps, as with the commander.
Wrangler 4D- the 4 dors make it like a GC, but has the same wrangler feel and structure. personally i dont like them. they look to long to be wranglers.
Wrangler 2D- great little vehicle to go to point a to b with all the off roading in between. they arent race cars, so they arent as fast as most other jeeps. the lack of space is made up with the ability to go down trails and in the woods.
Liberty/patriot/compass- all are on the smaller end of jeeps. they have the same function aas a wrangler, but are enclosed and they are more compact. (srry i dont know as much about them)
older models
Cherokee-
cross between a GC and a wrangler. they are small enough to be off roading, and big enough to tow, and hold kids and other things. i love them.. but the new liberties are like the old cherokees.and the patriot is like the old liberties.
93-98 JGC
i have one and i love it. the GC i have is a 98 and it has run smooth with no problems. im going into college and its reliable for the drive, and for the fun i want to have durring the summer lol.
99-04 JGC
little newer and bubbled loooking. but basic structure of the old grands.
all jeeps are good and reliable if they are properly taken care of. so durability is the same, but i think the older ones are better for the quality.
saftey isnt an issue, ive had 3 accidents w my gc and its still good, and it saved me in 2 as they were very bad accidents. they dont flip easily, unless u are turning 90 degrees at 70 mph. haha just dont fly into a turn or do anythig stupid and u will be fine.
i would personallygo with a grand cherokee or a wrangler. those are the models tht jeep has stuck with for a reason.
wow.. hahaha i hope i was able to help! good luck and happy jeepin. see u on the trail.