If you are asking about an R-21 classic .. should be no problem, but it of course depends on the condition of the cherokee and it's max tow rating. I'd recommend a heavy duty aux. trans cooler be installed. I towed my R-21 from San Jose CA to Lewiston ID with a Chev Astro Van (4.3 V6 auto, max tow capacity 6,500lbs) in very hot weather (temps as high as 113 deg) with zero problems and there are a few "good hills" between the coast and here.
My trailer also has no brakes and I never felt the need for them at anytime (the brakes weren't working when I bought the boat so I removed the seized calipers and rusted disks and pinned the actuator for the tow to ID and never replaced them...not required here for a trailer that carries "such a small load").
PS... Hi, Nellie May...I think you're the only R-21 I've seen that's the same color as mine!