I didn't have much difficulty inserting or removing the cups. I found that the super Jennie cups seemed to make it difficult for me to pee. When I had them in I could only get a very slow stream. They weren't that comfortable because I felt like they were putting a pressure on my bladder. I removed all of the stems and that helped a lot with the comfort level.
I only had leakage once on my heaviest overnight. I was using the super Jennie cup and woke up at 2 am to find I was leaking. I put it back in after cleaning and emptying it and woke at 6 am to find I was definitely leaking. I may not have reinserted it correctly since I did it during the middle of the night. Is it common to leak overnight during a heavy flow? My cup was not nearly filled when I removed it. I'm wondering if I just put it in wrong that time.
All in all I couldn't be more pleased with the cups. I think once I get it down it should work extremely well for me. Yesterday I didn't have any leaking at all with a medium flow and it was so comfortable. Today was my lightest day and I couldn't even tell I had the small Eva cup in. I found it pretty easy to insert and remove, and at most it only took me two tries to get it to open and in place. Not bad for my first go round!
I'm so glad to be off of disposables. I'm donating my disposables to a local women's shelter. I also bought some cloth pads from yurtcraft as cup backup and they just arrived today. They are so soft and well made and comfortable. I found I definitely need a liner or light pad as backup with my cup for the very thin watery discharge or just some remnants after changing.
Thank you to everyone who gave me advise on my first day of trying my cups!