I have the black medium classics in SHW and small black Chanel 22. The last time I used the classics flap was 3 years ago, and it's currently sitting in the closet. I use the 22 quite often. Just like what you said...When I go to places where I do not want to show the flashy logo, I turn my bag around, and it's a plain black hobo bag. How convenient it is!! Love it! I use the bag organizer and side protectors. It's very comfortable under the arm, and I have no complaint about the bag. I don't think I will sell the medium classics even though I don't use it much now. I may change my mind and will carry it later!
If you like, you can sell the medium flap and purchase the Chanel 22. Invest the remaining proceeds in the stock market, make some $$$. If you like the medium flap in the future, you can buy it again.