Newby and trailer questions

If you have bearing protectors you should keep them. I've tried it both ways; even with perfect new rear seals I would still end up with water in the hub after a launch without a pressurizing cap. You'll have water in your bearings every time you launch without them. As long as you don't overfill (max out the spring) everything will be fine.

From a popular manufacturer:
"Trailering, even a short distance, heats the hubs. When the wheels are submerged during launching, the hubs suddenly cool and the air inside the unprotected hubs contracts, forming a vacuum which draws in water through the rear seals. There is no such thing as a rotating seal that stays perfect. Water and grit thus drawn into the hubs relentlessly destroy bearings."

That would probably bo the case if the trailer was backed straight into the water. But since we have sail boats and it may take a 1/2 hour or more to get ready, I would be surprised if the bearings haven't cooled down by the time that we are launching the boat.

Bearing Buddies do have those caps that go over the grease fittings. I believe that this keeps the grease from getting all over the boat. My new trailer doesn't have bearing buddies but I intend to put them on before my next long trip.

I have a good friend who forgot about bearing maintenance, he had a bearing shear off on his Boston Whaler on a trip down to Montrey. He lucked out, he had just pulled over. Vincent doesn't sound like the kind of guy who forgets about maintenance. For me, I like the idiot proof bearing buddies.

One of the problems that my trailer bearings had was "bearing buddies" were not what was being used. The bearing cap just had a grease nipple mounted in the center.
Having looked at the "Bearing Buddy" itself, I like the idea of a spring loaded greasing system. It looks like it will grease the bearing properly and not force the rear seal out.

Took the Hobie out to the Delta yesterday, no issues pulling or with the trailer. Just the normal squeeks coming from the trailer bouncing over the road.
Was a little gusty, a little too gusty for taking someone out with me that had never been on / in a sailboat.