In my opinion, 5 squirts before each trip is way too much. It can quickly fill up and the problem I've had was that it gets forced out of the seal and into the brakes! The grease needs room to "breathe" and expand.
Bearing buddies are a good idea, just gotta keep an eye on them so they don't vibrate out. It's not a common problem, but I've lost 2-3 over the years that I had an open trailer. They are convenient because you don't have to disassemble everything to grease the bearings. But I always check them periodically to see if the bearings need to be snugged up. Too much play or regular looseness is a sign that something is wrong and that they may be on the way out. I jack up my trailer and check the brake and wheel bearing adjustment a few times per year.
Do you have one of these to pack the bearings?
http://toolmonger.com/wp-content/upl...0Composite.jpg
I have found a measurable improvement in bearing life by using synthetic grease. When I had a heavy open trailer, I was using Castrol HD grease. Switching to
Amsoil's Dominator Synthetic Racing Grease reduced the maintenance required.
My enclosed trailer now has the built-in EZ lube set-up.
http://www.floeintl.com/assets/pdf/e..._greasecap.pdf