I have both the classic jumbo and the celine trapeze. I took a side-by-side pic for size comparison
I use both bags as everyday bags, and love both. The trapeze is much more spacious - this bag can hold a lot! However, looking at your list of usual items, I think these things will also fit fine inside a jumbo. You likely won't be able to use a bag organizer inside your flap, because, as you mentioned, it would definitely eat up too much space. While the jumbo doesn't look too small on the outside, space inside is limited due to the more rigid structure of the bag. Nonetheless, I still find that it holds enough for me to use as an everyday bag. I don't think there is much that needs to be said for the classic flap - the bag speaks for itself.

It's classic, timeless and a staple piece in any collection. The trapeze is also, imo, one of the most artistic new handbag designs of the decade. It comes with a strap and can be worn on the shoulder, or on the crank of our arm or handheld.
I do, however, prefer the classic jumbo to the reissue 227 because the jumbo is a more structured bag. The reissue, with use, will flatten much more so than the classic jumbo. While this is all a part of the design, the jumbo as a stiffer bottom (newer jumbos also have stiffer sides) that prevents this from happening.
Either way, I think you can't go wrong

Let us know what you decide!