Grab your popcorn, this will get good!
-To recap, you've been towing a toad (not the wrangler, presumably something that needed the front wheels off the pavement to tow, on a dolly that had only breakaway brakes, but no (surge or electrical) service brakes? While that isn't really possible unless the service brakes weren't working (and subsequently the breakaway would also not work), you "were" comfortable with that setup but now questioning because you have a 4 down setup or a heavier toad, or just now learned that you may not have been as "safe" as you thought you were?
Just looking for some context.
FWIW, the "safest" solution is to have brakes on the toad and 9 of 10 rvnetters will tell you the same thing.
The real question is not for us to comment on and that is how safe is safe enough?
There's enough threads on this to choke a horse, where the best course of action may not be re-gurgitating all of that, but rather let you read the volumes of words already in print and let you decide for yourself.
2016 Ram 2500, MotorOps.ca EFIlive tuned, 5โ turbo back, 6" lift on 37s
2017 Heartland Torque T29 - Sold.
Couple of Arctic Fox TCs - Sold