New and in need of help...

[THEFERMANATOR]

You CHEROKEE will be fine towing it, just add a good size trans cooler and get the max cool radiator installed as well. This will run you around 250-300 in parts. Also get a quaslity trailer, this will make a night and day difference(good aluminum with brakes). I'm a former JEEP tech(car accident took me out of that trade) and can personally attest that THEY ARE TOUGH!!! I'm currently driving an 88 CHEROKEE myself and my last one was a 97 and before that I had an 88 COMANCHE pickup(notice a theme). I also have a 95 diesel SUB sitting outside, but the JEEP will do 90% of my towing needs. It's only real weakness is the short wheelbase, and around 89 CHRYSLER down-sized the brakes and they weren't the best for stopping.

I've personally towed with the 97 a WELLCRAFT 248 that was outfitted with with a bracket twin 225 EVINRUDE loopers and 200 gallons of fuel onboard. Pulling it wasn't the problem, STOPPING WAS!!! Hence why you really should have trailer brakes. We also towed a PRO-LINE 231 cuddy with it as well, same scenario.

Upgrade your cooling system to take it, if you have alot of miles do the shocks and such and use a good trailer and you'll be fine. But that's just my opinion. As far as the boat goes, I'm still rebuilding my engine.

ON EDIT: I wouldn't trade up to the grand to tow a V-20. The wheelbase is just as short and the only advantage would be the option of a V8 unless you went with the 99+ which finally got larger brakes than the CHEROKEE had(the early body style G.C. used the same basic brakes as the smaller JEEPS). And the old WAGONEERS will eat you alive in fuel costs.