I'm getting a fair amount of leaking, but to be honest, it's probably no more than what I got from using tampons - so I can totally live with it. And I'm hoping as I get better at inserting the cup the leaking will reduce.
Inserting and taking out the cup is getting MUCH easier already. I've learned to insert the rim of the cup just past my pubic bone and then let it glide up into place - sometimes with a little push from a finger and muscles.
One thing I realized I was doing WAY wrong at the beginning was taking the cup out. I was trying to get my fingers up far enough to squeeze the cup and take it out that way. Because my cup sits far inside, and it's hard to get around my pubic bone, this was not only very difficult, but somewhat painful. Now I learned to just grab a hold of the stem and gently pull down (with a little muscle help, by bearing down) until the cup is closer to the entrance. Then I give a gentle squeeze to the cup before pulling it all the way out. It also seems to be easier to remove if I tip it and let one side of the rim come out first.
Now that I'm feeling more confident I'm hoping things will just get easier!