A properly packed trailer bearing is good for 10,000 miles plus.
Don't squeeze grease in at every stop unless you have a bad seal and are leaking grease.
Bearing buddy's only grease the outer bearing, and
The grease will push past the seal and get on the brakes. I've purchased 2 trailers that had the brake drums full of grease.
Track your trip on a smart phone and post up. MyTracks or EveryTrail