i have the speedy 30 in monogram canvas and i too held off for a long time before i bought it. however, now that i have it i do not know how i lived without it. i love how chic it is (it definitely is a classic bag) and how durable it is (i feel like it is indestructible). i saw that the classic speedy is def a bag you need!
I love my speedy 35. I just got it 2 weeks ago. I find it so much better than the 30 size for me and I don't have tons of stuff in my purse. I am more of a shoulder bag but once I got this I am now thinking of what Speedy 35 I want next.
I do think it is hit and miss with bags and you can change your mind everyday. Can you go to a store and try on some Speedy's and see how it feels and looks?