If I had to hand sew bindings, I would not make quilts. Not becuase I hate hand sewing, but becuase it takes me so long to do it. Probalby becuase I am particular and don't want any thread showing where I've hand stitched if possible.
The number one thing I changed that turned binding from my most hated part (even machine sewing) into no big deal -is what Peckish said - do not press the binding in half. That one change resulted in eliminating all the problems I was having. I don't even need to pin the binding anymore.