Just had a quick look at that video link, Japhrimel - had to laugh at the woman daintily milking her breast onto a teaspoon - if I express like that, I shoot thin jets of milk several feet across the room!
mousey, things that have helped me express are:- warming breast beforehand (even just rubbing hands together and placing them on breast) - gentle downwards massage towards nipple before starting - and early on, I pumped either side of feeds, start and finish, on MW's advice, so I could gradually build up reserves without suddenly rocketing my supply.
I think it helps to do it regularly too, although I know that's not what you want to do. Just most things become easier the more you do it.
I do think expressing is partly luck of the draw. Some women seem to find it easy, some have a harder time - I spent oodles of money on a medela swing, and got virtually nothing with it, but with a manual pump, I get about 5 oz in 10/15 minutes or so. I also find expressing by hand almost impossible - very slow, and it involves a ridiculous amount of spraying. Nor can I feed one side and express the other side at the same time - there seems to be too much boob and baby in the way, and not enough hands.
All of which is just to say, what works for some people doesn't for others - hopefully you'll find something that suits you.