Re: Trailer tires...
RE: your question about bearings - Unless you're pretty proficient at servicing wheel bearings, just bring them to a mechanic and have them serviced. I'm told it really isn't a difficult task, but I've heard stories of bearings going out in the middle of nowhere and it's just not worth it for the cost of professional service. I have my bearings professionally serviced every year. I only tow about 1,000 to 2,000 miles per year, but they are always long trips (~300 mi one way) and have great distances between towns where I could get service if needed. It only costs me about $100 per year and it's worth it to me for peace of mind. I also touch the hubs every time I stop for a break to see that they're not hot. I've never had a bearing problem.
RE: tires. If you have any suspicion that the tires are getting worn - tread, cracks in side walls, etc. go to a tire store and have them replaced. If you're unsure, go to a tire store you can trust and ask what they think. Trailer tires - in terms of "boat bucks" are not expensive and again, for peace of mind, don't cut corners on tires. The same place can sell you a wheel and you can either buy a new tire for a spare or put the best old one on it. You can also buy wheels from any online source that sells trailer parts - whether it's a boating or trailer source (IBoats, Cabelas, Overtons, BassPro, etc). The mounting brackets are available in any boat store or trailer shop, also the same online sources If you can't find one before your trip, just throw the spare in the boat.
Make sure you have the right lug wrench for your trailer wheels and a way to jack it up. Don't assume your car jack and wrench will work. I recently bought something like this and it really works great, is cheap, and lightweight for easy storage on the boat:
http://www.iboats.com/Seasense_Easy...5599428--**********.538826120--view_id.237401