So after a few attempts at insertion across multiple days, I decided to read up on insertion techniques (and other posts) again and realized I was aiming in the wrong direction. Additionally I remembered to take it slow and breathe. I've now worn my cup for 3 days (for 9-12 hour periods of time) and have slept with it in. I've gotta say once I got the insertion and removal down (I'm better at not spilling) I've wondered how I never had one before. I do feel pressure from the cup and solved my "irritating stem" problem. I'm still trying to work out minor kinks, which I know will happen with time.
I did take it out tonight to clean and re-insert, but had trouble getting it to pop open after a few additional attempts. I decided to leave it out for tonight and try again in the morning. I have been using the fold down method and hadn't had a problem with my large fleurcup popping open before (had success about 6 times thus far). Any additional tips?
Overall, after a somewhat nervous start that "this might not work for me" I feel like it's been a success. I just wanted to share and thank the community for supporting me in this life-changing endeavor. Thanks!