*hugs* Amy...I think you're a wonderful mom
You should be proud of yourself for sticking with bfing!
As you know, I am pumping at work, and I will say that having a higher-end pump helps a lot. I also have a Medela Pump in Style Advanced ($300 pump, only paid half of that since I bought it off of ebay) that I've been using since going back to work vs. a Lansinoh pump I got when A was born (still retails for about $120). While I can still get milk using the Lansinoh pump, the Medela is much more efficient. Do hospitals in your area rent out their pumps, by any chance? That way you could see if your body responds better to the hospital grade ones.
I was also going to suggest buying larger shields to see if that would be more comfortable...sounds like you've already tried that.
As for encouraging your letdown, I completely agree that a huge part of it is mental. Often, I find myself having to relax my posture, take deeper breaths (I hold my breath when I'm tense), and visualize the milk flowing out of me like a stream...sounds silly, but it works. I get a letdown within 15-20 seconds of doing that.
Another tip for encouraging letdown is to lean over and slightly jiggle the girls. I find myself having letdowns even when I'm not feeding or pumping if I'm leaning over a lot during the day
Might I add that I think Anna sounds OT/OS at the end of the day and that while she wants to comfort herself by nursing or that she truly is hungry, it's just too much for her to eat. M will get like that if she's too OT/OS (more so with OS) at bedtime. She is so unsettled while eating and will cry and chomp down on me like she's full, but really she's screaming at me, "Just put me to bed, Mommy--NOW!" I'll then actually bring the DF forward and hope for the best for the rest of the night.
Again, lots of *hugs*. I know the whole ebf/ff thing can be a very sensitive issue, especially when us Mommies want to do right by our babies. However you decide to do things, we've got your back