I find the Lyle (
Amazon) works well and is handy because it stores the grease in the cup - just put the dust cover on the thing and set on a shelf for the next bout with the bearings. It appears
Harbor Freight has a similar one. These simplify things and reduce the mess somewhat. Some just use a ziplock bag while others are into the karma of a handful of grease being worked into the bearings with love and tenderness ( ;-) ) - some greases could almost work as hand lotion...
The Lyle says it can be used in a bench press to push the grease through the bearing which might be an idea if a bit of pressure by hand is a problem.
I usually clean bearings with diesel or kerosene and then final clean and inspect with brake clean (spray can). Only when I have clean bearings that pass inspection do I load them up with new grease.
Around here, the bearing pack schedule is 2 or 3 years. See
Bearings - which will get an update this year if everything turns out as planned.
The bearing seals have an interesting variety, too. I use single sided double lip that
LCTP sells for less than I find most elsewhere. (they seem to be down for maintenance right now, though. The local auto store wants an arm and leg for 'em.