Since we store the boat in an enclosed storage unit I invested in an air compressor to keep with the boat. It's great to be able to inflate trailer tires completely before every tow without hauling an air tank around. But since I already had the compressor, I also bought a pneumatic bottle jack. I can put that under the end of an axle, squeeze a valve for a few moments, and that tire is off the ground - walla.
I also have 4 jack stands that I use. I covered the tops of the stands and the top of the bottle jack with several thick layers of Plasti-Dip so they won't tear up the paint on the trailer. Works great.
As far as rolling the wheel while pumping in grease - as long as the bearings were packed properly when they were installed and you're only topping off the hub, rolling the wheel isn't as important as you might be making it out to be. Good practice, sure - but you didn't hurt anything by not doing so.
