I have the small (now called medium), and it will be a very tight fit for your items. The flap is not my issue. For me, the issue is the divided sections which you end up with two little sections. I find the middle zippered section almost worthless except to hold small items. If you have a huge eyeglass case, it may be a challenge to push it in because the bag design is a trapezoid, so the top opening is narrower than the bottom and the top opening is not that flexible due to the stitched center compartment. I would definitely purchase a bag that offers a refund. To me, I think you’ll be on the edge of usability. As FYI, I had this big
Prada eyeglass case, and it was super hard to stuff in and get it back out. I switched to a soft nylon pouch and it worked fine but I had to adjust.
One other item is the handle. The drop is very short, and the handle is a bit stiff. I hand carry mine so it’s not an issue. However, the few times I’ve had to stick it through my arm, it was not really comfy as the handles are round and stiff, not flat.
I love the CH and have been using them a lot now (I have a black and a green). I thought this would be another bag I could collect, but no. My big deal breaker is the divided sections which make the bag a bit not usable for me as I cannot carry a small water bottle as it takes up the entire depth of the bag after I push it in. So, another adjustment to use this bag, and only recently I realized I’m sacrificing too much for this bag. I recently just decided no more CCHs for me unless it comes in a jumbo size that is wider (not more height or length).
I carry... mini o-case, lambskin classic card holder, small hand sanitizer, pack of tissue, eyeglasses, a few masks, two lipsticks. I put my phone in the outer pocket.
Hope that helps. Good luck!