You don't need special tire tools like a bead breaker. Unlike a car wheel, the halves of the aircraft wheel pull apart when the thru bolts are removed.
The main difference between aircraft bearings and auto/trailer bearings is the lack of a watertight seal on the axle. Boat and car bearings have a double lipped rubber seal on the inner axle, while our planes just have a felt ring. 99% of the time when a boat or car axle fails, it is because the seal failed and let water in.
I used to tow my boat a lot. 500 mile trips on the interstate at 70 mph. Combined with dunking in the ocean weekly, that is a very demanding environment for bearings. The slightest salt water intrusion into the bearing will cause corrosion and failure, which melts down the bearing and destroys the axle in spectacular fashion, usually on a Sunday night in a rural area. So if you are serious about trailering and you operate in the ocean, you repack your bearings every year or you eventually learn your lesson the hard way
But an airplane is not a boat trailer. For a hangared aircraft flown in fair weather, you could probably go 10 years between repacks without problem. Having said that, those bearings do not have a watertight seal, just a piece of felt to keep moisture out, so they do need to be greased on a regular basis. As Bob points out, bearing failure in a taildragger is a non-event, just some extra noise.
Boat trailer bearing hubs are an unholy mess. I've tried just about every possible degreasing substance possible. IMO the best is mineral spirits. Toss in a dish, let soak for a bit, then clean out the nooks with a parts cleaning brush, blow out, hit with a shot of brake cleaner to dry, and repack. Do not allow the bearing to spin if you blow out with compressed air.