OK, Bass boat is 3 years old, I have never thought about the bearings on my trailer.

Saw some red-eye bearings at wally world and wondered... Have I been forgetting something?

Yeah you need to lube the wheels. I try to remember to do that at least once a month depending on how many times I go fishing, may be more. I especially do it on long trips. Neglecting them can lead to some problems when you are towing your boat.

You need to really think about getting them serviced right away. Lubing them through the bearing buddies or red eyes only keeps them pressurized to keep water out. I would remove the bearings clean and inspect and repack, or replace. Then once a month give them a squirt through the bearing buddy/red eye. Remember, an ounce of prevention is better than a pound of cure. You don't want to have a bearing freeze up going down the road.

It's a very sick feeling in your stomach when you see a wheel/tire passing you, gosh that look's familar, then you notice the sparks from the trailer.

Sounds like you talk from experience Flatfish

Wheel bearings are EXTREMELY important to take care of.  I bought a used boat a few years back.  When I would jack the trailer up and spin the wheels you could hear grinding.  I replaced the bearings and races, but it took a machine shop to pop two of the races out of the hubs and they had to break them to get them out.  It was almost like they were welded in.  Monthly greasing through the bearing buddies will save you alot of headaches down the road.  Even using bearing buddies, I still repack my bearings every two years.