So I wanted to post my own success story. I started using a cup in some form 3 years ago. I had a small Mooncup U.K, which is pretty much the easiest cup to open and seal, but a bugger to fold. I had some leakage issues, so switched to a Large Lunette, which I found uncomfortable. Then I tried a small Diva, which I couldn't get to open and it leaked.
Finally, I switched to a small Pinkcup (pink Ladycup) and it's been plain sailing. I should have got the smaller size according to their guidelines, but it works fine on the first day of my period. I'm very very sensitive to internal pressure (I tend to involuntarily clench my vagina when I have cramps) on the first day, so the really small Pinkcup helps catch the blood flow without hurting too much. On the second day when the cramps ease off (I get cramps 3-4 days before my period starts and they normally ease off on the 2nd day of bleeding and stop completely by the 3rd day), I use a large Diva which means I have no leakage issues and it deals very well with my heavy flow. My flow goes; day 1 - medium-heavy (frequent emptying of small Pinkcup), day 2 - UBER HEAVY RED RIVER FLOW which would soak a regular uber thick super plus tampon in about 1.5 hours or less, day 3 - heavy flow, day 4 - medium to heavy, day 5 - light and day 6 - spotting. I find the large Diva easier to fold, insert and open. On the light flow days I can normally just leave it in for about 8-12 hours and not change it very often. I forget it's there most of the time :-P
So as you can see it's been a bit of a long haul. I managed to get rid of my cups by uber cleaning and uber sterilising them and passing them onto a few more open minded friends who uber cleansed/sterilised them again to be on the safe side. I know that the idea of used cups freaks some people out, but they were barely used and I didn't want to see them go to waste!
I'm glad I've finally found a cup/cups that work well for me, I could never go back to tampons ever ever ever again. I remember getting stuck in a really dirty bathroom with no running water and being too squicked out to put my cup back in, so I used my emergency tampon. I felt really uncomfortable, dry and sore for days afterwards. I love the cups and the fact that they're silicone means my latex allergy doesn't get irritated either.
I get less leaks with the cup (like zero leaks) than I did with tampons and my vagina is healthier. I'll save a lot of money in years to come. Despite having bought/owned every cup to woman in the last couple of years, considering my flow and the amount of tampons/pads I used to go through, I've probably still saved a considerable amount of money, I just haven't tallied it up.
I do get a tiny weeny bit of leakage on the first day when I use my Pinkcup because it's small, but it's easily absorbed by a panty liner (I make my own).
Although it's been a lot of effort, I'm so glad I made it! There is absolutely a learning curve to cup usage, but then there was a learning curve to pads and tampons for me too! It took me ages to find pads that were the right shape/size/thickness for my flow, and to find ways of stopping them from bunching up and rustling. I couldn't use applicator tampons for ages because I dumbly just couldn't figure out how they worked (duh) and used the Lilets non applicator tampons which felt like candlesticks in my bajingo :-P So I think making the effort in order to save money, the environment and your vagina is definitely worth the effort!