I don't have an answer for you, but am curious about emptying the breast--what do you mean by that? Because they're never really empty, they just have less and need time to make up more.
You're not dumb!
Pumping drove me absolutely up the wall until I upgraded to a double electric pump (Medela Freestyle, NAYY). I had been using a Phillips Avent single electric but it took forev'. The hands-free component and double pump made it worth the money. I pumped while putting on make-up in the morning, and even very carefully while putting lunch together. It infinitely helped that DD was over 6mos and that meant she didn't need strict attention to detail on sanitation, since she was eating solids that were cooked but weren't germ-free on clean but non-sterile plates etc. I could afford to rinse the pump parts with water after pumping and not have to sanitize every time. I boiled the parts once every evening before going to bed and let them air-dry, then kept the milk chilled between sessions in the Freestyle's portable thermal pack. It was refrigerated and drunk the next day so we didn't need to be extremely careful to make milk suited for longer-term freezer storage or something.