Gobbling the more the better. Remember that centrifugal force will move grease away from the center. The more that is there, the better.
Typically, after packing the back bearing, and dropping it in the race, I put more behind the bearing all the way around, and then the outside where the seal sits, then install the seal. On the outside bearing, gob as much as you can before putting in the outside bearing.
I have the same mixed feeling about buddy bearings, and have mix success. It is probably better for boat trailers where the axle is submerged.
I have never pushed a seal out, and the spring on the inside of the seal keeps it tight against the axle.
Also, I used some premium priced environmental grease from Tractor Supply (its sold other places too). It was bad. Burned up two bearing sets and hubs before figuring it out, then cleaning it out of everything and went back with a quality high temp, high speed grease. Synthetic is good, but stay with a quality company like Mystic. Personally I like a colored grease (not black) so I can see how it performing. If it keeps it color, it is good.
When you are broke down on the side of the road, its time you could be jeepin.
Hope my opining helps
Ride Hard, Tread Lightly