I had a similar thought process to you before I purchased my first Chanel! I went from wanting a mini (couldn't get past the lambskin too) to the small CF to thinking "I really want a classic piece" which led me to purchasing a M/L classic flap at the beginning of the year before the price increase!
I carry my Chanel card holder, LV key cles, a mini O case that is serving as a catch all for my small items (lens wipes, travel size perfume, compact mirror, and eye drops), and my iPhone 12 Pro. So I'm sure the items you are planning to carry will fit inside! I just ordered a Zoomoni organizer so we'll see how everything fits with it.
I believe the medium has a shorter chain drop than the small. I am 4'11 and personally don't like the look for the double strap on me but the chain drop is perfect for me! I definitely don't feel like the size is overwhelming for my size.

I carry my Chanel card holder, LV key cles, a mini O case that is serving as a catch all for my small items (lens wipes, travel size perfume, compact mirror, and eye drops), and my iPhone 12 Pro. So I'm sure the items you are planning to carry will fit inside! I just ordered a Zoomoni organizer so we'll see how everything fits with it.
I believe the medium has a shorter chain drop than the small. I am 4'11 and personally don't like the look for the double strap on me but the chain drop is perfect for me! I definitely don't feel like the size is overwhelming for my size.
