You can probably find quite a bit of more detailed info in the Search... but a lot of guys do the regrease and the bearings last a long time. The one thing you have to check is if you have the regreasable bearing. Some bearings sold by the Canadian Yamaha dealers were not regreasable, meaning you can't get the seal off. But if yours are regreasable, then after you remove whatever is in front of the bearing, get under the lip of the rubber seal with a dental pick or small screwdriver, gently massage it up and loose so you don't bend the bejesus out of it. If you have air, I use about 50 psi while holding a rag over to catch the grease, and blow the old grease and moisture out. Then I apply any good bearing grease with a needle, pointy, or regular tip grease gun, doesn't matter because you have to push the grease in with your thumb anyway to get it to the back, and it will get back there if you press it in, because I've checked by doing it on the bench. So yes, one side is good enough. Ideally do it at the end of each season.