So I wanted to post about my positive first experience to reassure people who are considering getting a menstrual cup. Once I found the fold that works for me (origami), it was super easy to get in. Removal is just a little bit harder, but I can do it in a minute or two and it doesn't hurt or anything, and it isn't that tricky. In fact, I just tried removing it while sitting on a toilet and had no problems, so I think that if I needed to, I'd be able to take it out in a public restroom (which was also something that I worried about). And this is only my second day ever of using a cup!
I wore it last night through the night and was a little afraid that the cup would ride up too high for me to get it out in the morning, but nope. It stayed in one place with the stem just barely poking out so I am able to grab it and get it out without too much trouble. It is a little bit challenging to break the seal, but like I said, I'm still able to get it out with no pain in just a couple of minutes (which I think is pretty good for this being my first time using it!) Also, there have been no leaks so far.
So, to everyone who isn't sure yet if they want a cup, please try it out and don't be afraid! Some people do have problems the first time, and there's definitely a learning curve, but there's also a chance that you won't have any problems.
(Stats about me: 23 years old, married, former tampon user)