When we recently did the oil change on my B3 the mechanic didn't have his handy dandy shop pump with him so he used my el cheapo hand pump that screws onto the top of the new oil bottles. I hate them but he was perfectly happy to utilize it and it worked very well . (I'm not using the Merc green oil btw)
A little trick he did was to take the reservoir in the boat out of its mount and turn it upside down to help delay the onset of gravity fed oil rush .
Yes, it's all about being prepared and moving quickly . Have the drain plug and a new o-ring ready to go beside your foot and move fast !
There will always be that annoying dribble though .
Just because something's old doesn't mean you throw it away !