I don't normally comment but I just saw this thread and thought I should as I was "complaining" to my friend on Saturday that I like my WOC too much.
I've a 227 Reissue, black with silver hardware, which I always believed was my dream bag and it is a great bag, I can fit a paperback novel in it, I've even done an overnight stay with that as my only luggage and I can fit my phone into the outside pocket but at the moment it's playing second fiddle to the WOC.
I got my WOC in November basically on a bit of a whim, it popped up on Vestiaire collective for a very good price (and there was a Black Friday code and cashback too) and I thought I'd treat myself to an evening bag for the Christmas season. It's also the Reissue model in black but with gold hardware.
At the end of February I went to Berlin for a weekend with the girls and I brought the WOC, but I ended up using it during the daytime too and frankly the 227 has hardly had a look in since (which I feel horrendously guilty about).
The WOC is tiny but it's so well designed. Before I got it I watched a few YouTube videos where people try to put a purse in it and then declare it's too small. But it's already a purse, that's why it's a Wallet on Chain! My phone fits in the front pocket (and it's big - it's a Samsung S9+), there's a zip pocket where I put my coins and notes - admittedly I can't really get the coins out when the phone is in the front pocket but I hardly ever spend cash anyway, there's another pocket where I stash receipts, business cards I'm given or a shopping list if it's not on my phone. Currently in the main part of the 'bag' I've got a pen, my headphones, a power pack (and cable), a mini tube of suncream and my sunglasses (before it got hot I was carrying a folding shopping bag in it). The 'love letter' pocket I either use for emergency cash, a spare pantyliner or a couple of pieces of paper if there's any risk I might have to take notes. It has 6 card slots which isn't a lot but I've got quite a few loyalty cards stored in my Google Wallet, but the best bit is that the back pocket perfectly and securely fits a credit card which means I don't have to even open the flap I can just grab the card out the back (and as pretty much everywhere has contactless now I use it for all the low value spends too, hence cash being redundant).
The strap is also long - so it's a really good cross body bag (although I'm only 5ft 1in) and because it's slim, it sits really close to your body so you don't worry about knocking people with it, fitting through doors or having it snatched off your shoulder! It's lightweight and your hands are free. I've even worn it underneath a long coat a couple of times (in places where I was wary of pickpockets) without it feeling awkward. The 227 can theoretically be worn cross body and I have done that when I really needed both hands but it sits too high, sticks out awkwardly and it looks like you're stretching the bag, so I always carry it as a shoulder bag with two straps which is fine but not as convenient as the cross body. Conversely you can carry the WOC with the strap doubled over so it looks like a little flap bag but in practice when you open the flap the chain unravels, so it's just annoying.
As for price - I was in Chanel Bond Street at Easter and there was a gorgeous blue seasonal WOC for just under £2000 - I think the classic ones are usually less, so maybe £1700. Is it worth the money depends entirely on what you're comparing it too - at present I'm definitely getting a better cost per wear from my WOC than from my 227 which I think is currently around £5000 new.
So if I've not made my point clearly enough, I love it - I only wish that, if I'd known I'd use it so often during the day, I'd have not gone for gold hardware.
Hope this helps! There are plenty of YouTube videos of people showing off their WOCs and comparing them to their flaps but really the only way you're going to know if it's right for you is to head down to a boutique and get your hands on one.
Good luck!