What is the perfect size and color for the Chanel 2.55 reissue?

I am on the verge of getting the black Chanel reissue in medium. I think it is a good size for transitioning between day to night. Also, the design of the bag seems to ask to be smaller, and not bigger, it wants to be petite and delicate. However I am willing to hear opinions on this. Perhaps some of you have it or the large and can tell me what fits inside... etc. Also, I am on the hunt for the gray color. If anyone has had any sightings.... Much love to all you bloggers!
I have the re-issue in black, I think it's a 227( 12 x 9 in diameter).I guess it's the medium size. I'm only 5 ft but it doesn't look big on me at all. I could fit a lot of things on it ...my wallet, cell phone , date book and more. With regards to color, I'm partial to black, that's why I chose a black one...though I think the grey one is beautiful also.
Ooopps, just realized that mine is actually considered a large one. From what I read, it comes in 4 different sizes 225(small), 226 (medium), 227(large), and 228 ( jumbo?). I got this info from TFS under Chanel re-issue.
In my possession at this very moment I have a black 226 and a grey 227. We are giving my mom probably the black one (her choice, but I know she'll pick it) and the other one a) will be returned to NM, or b) I will keep because I can't bear to return it! I'm 5'8" and I don't feel that the 226 is too small on me but I personally prefer the 227. I could do either but I always choose large bags. Choosing the COLOR, that's the problem. The grey is so much more special but boy I'd have trouble working it into my wardrobe. I think it's adorable with jeans and whites or light neutrals... my problem, I always wear black!
This is what I am thinking:

Coco Chanel originally had the medium sized bag. She never made the large, jumbo or small. So the medium has some history. Also, the medium says, "Wear me at night or day, I can do either." While the large says, "Day only please!" and also reminds me a little of an art portfolio case. However I am one to enjoy not worrying about what can fit and what can't. I want to take what I want to take. Period. So, for that reason I struggle. I also find the black and grey to both be very pretty, but I am thinking that perhaps the grey is more "youthful and fun"? While the black is more elegant and serious? Am I insane here, or? Anyone have pictures to share?
I personally like the 227 model. It probably isnt evening bag material, but I think could go well for a night on the town. I love the white! The gray would probably be easier to take care of though. My SA said that some people had problems with color transfer on the white.
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i'm falling deeper and deeper in love with the grey reissue in large... my guy is getting jealous of my handbag fetish.. sigh. i want. but no $$$
I think the large(227) is the perfect size. I'm 5'2" so I was worried that it would be too big but it's actually a great size. I also would pick the grey first because you can always buy black in the regular 2.55 but none of them will be in this shade of grey. Here's a pic to show how the large grey looks on me:


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I had a white Reissue in medium and returned it. It was small for my day to evening needs. I do, however, own the large 227 in black and I love it! It's very roomy, classy, and you're getting more leather for the money. I guess it also depends how much you carry. You can't go wrong in either size as these Reissues are beautiful bags.