I know prices are higher in the northeast. I just picked up an '02 Jeep Cherokee Overland, 4x4, 61k miles, High Output 265 HP 4.7, leather, loaded and perfect condition, brand new magnaflow exhaust and a brand new set of BFG A/T tires on them that had to have just been put on. KBB retail of $16,995, asking price was $14,995 and I got them down to $11,250. I'm on a few Jeep forums and the northeast guys are going nuts, say they can't find a cheapy I6, Laredo 4x2 in decent shape with under 80k milesfor near that! One guy was so adamant that that deal couldn't be true that I scanned the bill of sale and PM'd it to him...
The sunday paper here has an entire section dedicated to auto sales here, I'll bet I find at least a dozen advertised Rams right at or near the prices I gave to you offone dealers website earlier.

 

I'm in Central AL. Here fullsize 4x4 extended or crew cab pickups are the hot ticket. That seems to be the case for all of AL, GA, MS and a large chunk of TN. Get out of that region and prices like you mention can be found.

Grand Cherokees are dirt cheap.

Go figure.

You mentioned you're in centeral FL so I plugged an Orlando zip into Auto Trader and found plenty in a 300 mile radius like you mentioned.

Jeep CJs and Wranglers sell good here. Guy behind the counter at a 4X4 shop offered $1,500 for my '85 off my description alone. And I was brutally honest about its rough condition. Didn't have the heart to tell him all I had in it was $500 and my cost to go to upstate NY and tow it back:

 

Price seems a bit high. I got mine for $11,500. But it depends on the part of the country too, Hammer has insane prices there. You can't find one for close to that here in the northwest.

I like my '02 5.9L. It does just fine for what I use it for. For that price I would probably try to find a Hemi though. For gas milage I average 12-14 mostly around the 13.4ish range. And that is with some towing and quite abit of city driving. But I also have an aftermarket exhaust, superchip, TBS (don't know if it really helps) and a jet chip module. I like the power, have been happy with the towing that I do (4000lb boat). Its been a good truck so far.