If/when you do decide to come back to this, I wonder about starting with tampons? Just because they're cheaper and people seem to find them to be more simple than cups (maybe?).
This may be slightly TMI but may help someone: one of the things I did was practice inserting a tampon when I was not on my period, so I could get used to the process and the feel, and deal with any reactions. I did this by starting with the slimmest tampons and using a lot of lubricating jelly (if you aren't menstruating you need something to help the tampon slide in). I'd stop at various points and hold it there if I got too overwhelmed, and just saw how far I could go each day. Once they were inserted, I left them in for 30 seconds to a minute to keep working with my anxiety. You definitely do not want to leave tampons in your body when you are not on your period.
If you go this route, be warned that while I think I was doing it safely, I did not have this plan approved by any sort of medical professional.
