This is one of those topics that will bring out strong opinions about how you need to disassemble and clean the bearings annually, and if you use a grease gun you'll blow out the seals at the back.
Here is my opinion: I use a grease gun, but I am cautious about how much grease I give the fitting. I give each fitting two squirts, then the next day another two squirts, and so on, so the grease can migrate and take off any pressure from the seal before it can start to leak. When clean grease appears, I'm done. It has worked for me, and I've pulled my trailer 20K miles over three years. Another option is to grease slowly while rotating the wheel. For sure, you want to hand-grease, never power grease, and I'd say it should always be done in warmer temps, not in February, so the grease flows well.
BTW, the quality of the grease is very important. I don't recall the specs and I'm far from home, but you can't buy too good grease. There is a Lucas Oil place in my town, and I buy the best they have for wheel bearings.