As for boots, I just push them in the best I can from the top, and then crawl under and tug the lip into place. It is a PITA at first, but it works. A BL is a help, but I can imagine you could do it without, just hug the tranny and use both hands.

As for getting fluid via other manners, for topping off, I will use one of those screw on on/off thingies with the long tube on it. Put it on the bottle, get it into place, lift the bottle as high as possible and then open it up. Squeeze until the bottle is empty or the tranny is full.

I found the pumps to be a royal PITA, plus they are a mess to clean up afterwards.

Good Luck,
Michael