The beast will pull it, no doubt, reallly depends on the distance and your comfort. I occasionally pull a 24 ft Pusuit up to 50 miles with no problems with my '95 5sp. With the boat, trailer, fuel, stuff probably close to 8000lbs. I'm near the coast in NC so its flat but I have to keep it no more than 55 and have to stay in 4th. Actually get 11mpg towing. The front end feels a bit light with that much weight. Combine that with the short wheel base and you won't want to drive fast, but under 60 and it's fine. Braking is not a problem but needs to be planned for. As far as hills, you will definately feel every slight incline/hill.
Not sure on that one. I have trailer brakes on mine. I do also have a small sailboat on a different trailer that I occasionally pull as well. Probably 3,000lbs, maybe a little more, with no trailer brakes. I haven't had any issues but your looking at more weight than that with a very short tounge on the dolly as well. You can always do a test run just to see how she behaves or rent something bigger.
You will be fine.. I use My RRC to pull my 65 dodge pick up all over... I have also used it to pull a toyota 4-runner from Illinois back to Colorado... Not to mention all of the camping etc.. I do... You will be just fine
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