Dad and I did it twice (once going in, another going out when sold) with our 23' Sharkcat mate. Ratchet strapped the trailer very securely to the boat with special attention paid to no allowed fore/aft movement and motored at idle around to the ramp. Distance of a few klm.
We DID have a sturdy dolly wheel bolted toward the front of the trailer though, that helped when approaching the ramp and stopped the coupling of the trailer striking the ramp. Not sure how your trailer is set up? Our required that on the ramp because the ramp transitioned from around 10 degrees to 20 degrees as it was winched up toward the house.
A mate then used our ramp and did the exact same thing with his 24' Savage flybridge.
You other option is to float it out using some 44 gallon drums without the boat on it. Either way its a bit of fun and an adventure
Shouldn't worry the bearing unless the seals are already buggered. They go underwater when launch/retrieved anyway.