This coming spring, Im thinking of retiring my 15yr old GM SUV for something newer. I really like those 2nd-Gen Grand Cherokees (99-04).
Since the 01’s and newer ones are still expensive even used, Im looking at low-mile 99 & 00’s. And I have lots of questions:

.1- Are there any common problems I should be aware of?
.2- The 99’s are first-yr-change models, any bugs?
.3- Im looking at 4.0 sixes, I drove 90 Cherokee with this engine & was pretty quick. Is the heavier GC any slower? Is the 4.7 V8 much more powerful.
.4- My GM with a 4.3V6 only gets 15/19mpg (city/hiway) what kind of MPG can I expect with a 4.0 (or with a 4.7V8)
.5- Are there any easy, legal performance upgrades, like chips, headers, air intakes, etc?
.6- How durable are they? I don’t do much off-roading, but the roads here near NYC are horrendous on their own. We get a few good snowstorms, and there’s constant road construction & flooding.
.7- What about the super-expensive things like, ECM, Airbags, ABS-controller, Climate controller, fancy elec stuff, etc?

Last, how are there compared to the 1st-Gen GCs? Would I be better-off with a low-mile 98? For some reason I see A LOT of used 96’s? Was that a good/bad year?

Be brutally honest, Thanks...

Well, I won't be able to tell you much, but I'd certainly like to point out
one thing to look out for. I'm also from NYC. I picked up a '99 Grand Cherokee LTD. 4.7 V8 this past summer. A/C was working fine. However, when the weather got colder later in the year, I realized I couldn't get any heat whatsoever no matter how I set the climate control. I later found out about the design flaw in these '99-'03 Gr. Cherokees in the HVAC system...the blend doors which control the amount of heat entering the cabin are notorious for breaking down and remaining in the closed position...hence, no heat. It's a very time consuming repair and runs around $1000.00 - $1200.00 average to repair, I have learned. I'm using an auxiliary heater until I can get this done. So, I suggest you check the heater thoroughly, on various settings, before you buy one of these. Also, ask the seller if he ever had this repair.

I'm averaging 12/17 mpg. (city/highway) I have no complaint about the power on my V8, it seems very strong, downshifts quickly when I'm cruising and hit the gas hard. Takes the bumps well with tire pressure regularly set at 32 psi all around, with 2 occupants and no cargo. There is that annoying side to side wobble which I understand Jeeps are known for during aggressive cornering. I haven't tackled any really inclement road conditions yet. Nothing else major I can point to in my case, so far.

Good luck!!!

Bob