Any ideas on how to get my TT from Wisconsin to Florida?

Any suggestions you get are hit or miss. Hard to troubleshoot something via words without seeing or feeling it first hand.

Given the only variable that has changed (other than the trailer), is the transmission, that's my bet. Sure, it was done by a reputable shop, but they can mess up too. Nobody is perfect.

I suppose another option to get it home could be to rent a truck and haul it home, then fly back up and get your van. Still doesn't fix the van, but gets your trailer to Florida.

Mike