Chanel Opinion Needed

I'd keep the classic flap and patent bowler 'cos I'm not exactly crazy over the medallion tote. The medallion tote is a classic piece so it'll be around if you want it again; the classic flap (although always available too) is more timeless and iconic than the medallion. JMHO.
 
I agree with your decision to keep the flap and bowler. You can always get another Medallion Tote but the classic flap will be more expensive to purchase again and the bowler is no longer available. As for who to sell it through, I think ebay is your best bet since there is so much exposure. If not, look for a local consignment shop in your area. They also sell Chanel bags.