I was on the same boat a few week before. I just bit the bullet and bought Classic caviar medium flap in Black with SHW yesterday. (Reissue 226 is still on my wishlist
....it may be in there for a very long long time)
For me $1700 is still too much for WOC. I know the Classic flap price is more than double that (even more so for your reissue 226). These styles, however, are classic and will be with you forever. I think you can get more use out of reissue than WOC. I can wear mine day/night, both side and crossbody (I'm 5'2", 118 lbs). When I put strap inside, I can get away with it as a clutch too. I know myself if I got WOC first, I wouldn't settle for it. I would still yearn for the classic. That's my 2 cents though.