I've launched with the TC loaded but most of the time I drop the TC because we are staying in the location for a while like when we go dipnetting or sport fishing on the Kenai River. City Dock is built for launching and a really nice facility. Some of the other ramps not so. Having four wheel drive and the diesel makes the job easy even with the TC loaded.
It sounds like you don't trust your Caribou's jacks since you have to pack the saw horses. That does complicate the process. You don't say but I'm guessing you have manual jacks that further make the process a challenge.