i guess it depends on the reasons you own a truck and the reasons for wanting a Jeep. if you own your truck because you need to carry stuff now and then, then skip on the Jeep. if you want something to offroad in, then go with the Jeep. i love my Jeep, it's my daily driver. that being said, i have two complaints: gas and storage. it's a pig on the road, your truck probably gets better gas mileage, and, other than passengers, there's not much room for anything else (you have to utilize racks and trailers). don't get me wrong Jeeps are awesome, they're fun to drive, they don't follow KBB, there are a ton of aftermarket modifications available, and you'll instantly be part of a "club."
if you do decide to go for the Jeep, be weary about the Jeep you're looking at. TJ (1997-2006) is definitely the way to go. the 4.0L I6 is an awesom engine, not a lot of horsepower (190hp @ 4200), but plenty of torque (235 lb-ft @ 3200). they are durable, when well maintained, will reach 250K. get the automatic if you want to do some crawling, though majority of Jeepers swear by the manual (the manual will give you more power due to direct coupling through gears versus fluid coupling through a torque converter on the autos). the part to be weary about is the lift. most dealers will lift their Jeeps for looks and not functionality. unless that Jeep is a Rubicon or has aftermarket axles, 33" tires is pushing the limits of the Dana 30/35 (offroading applications). most likely, the differentials aren't re-geared. i doubt they bothered installing a slip-yoke eliminator and CV driveshaft. hopefully, they installed a HD steering. depending on the size of the lift, the stock control arms are good up to 4", then i'd recommend a long-arm kit. because it's lifted, both track bars should be replaced with adjustable ones, there are brackets available, but those just put more stress on the components. all this doesn't apply to the Rubicon. once again, the dealer just made it look good, unless the previous owner put in the wrench time, then you have to wonder what kind of abuse the Jeep has seen in 9 years and 100K miles.