Kelney, about two months ago I was pulling my boat down from Yuma and my entire hydraulic/surge brake drum assembly/rim/wheel came off one of the wheels on my boat trailer (I assume I blew a bearing which must of then put pressure on the retaining nut/cotter pin), so I had to limp into Rocky Point/Safe Marina on 3 wheels instead of four. I'm anal with maintenance too and regrease my bearings after each use. Even tough I had a spare/jack/tools there was nothing to attach it to, since all that was left was basically a bare axle. While we went fishing the next few days the guys at Safe Marina contacted someone local and he installed a temporary rim (but without a brake) so at least I could put my spare on. Contact Miguel at Safe Marina, he can hook you up with someone local if you'd like, in fact I think the guys at Safe Marina can do it themselves, they're real good and reasonably priced at stuff like that. In the meantime I ordered a new hydraulic/surge assembly for my trailer and installed it myself a couple weeks ago, I keep my boat stored at Whale Hill now. I have to go back shortly and manually repack my other bearings, even though I have Brake Buddies I still want to inspect/repack each wheel manually so if you don't wanna use Safe Harbor I can do yours someday, no charge, we'd just have to figure out a time to meet. It's really no problem and doesn't take long, I have all the jacks/tools. I try to make it down to Rocky Point once a month.
I don't know how old your trailer is but you can buy new pre-packed bearing kits for real cheap, they include inner and outer bearings and seals. Lots of places online like westmarine.com sell em, you just have to know what size your drums are, if you take your tire/rim off there's usually a number stamped on your drum and if you google that number you can determine what size it is (ex 10 inch, 3500 lbs).
James