I wasn't good at it either lol. It took me about a month of squeezing every few hours to get any results. And then it was awkward. I'd bring my stool and bottle into the bathroom. Then I'd sit on the toilet, put my feet up, prop the bottle between my knees and milk like a cow. Oh the things you do for love...
I was never good at that.
Sorry I'm not much help. I pumped by hand, literally lol until ds was a yr.
It really depends on your situation and how often you plan on pumping. If you sah and just need the occasional bottle so someone else can watch baby a manual pump is probably fine. If you are working part time and need to pump I would say a single electric would be good. If you work full time and need to pump often you may want a double electric. I prefer medela pumps but have heard good things about others as well.