I did a massive clean-out this year (and still am planning to pare down a bit more) and sold the following:
4 keyfobs/charms
4 scarves/other accessories
9 Coach bags
5 non-Coach bags
...I still have a couple of items that I want to sell, but am trying to get the timing right! I'm not sure anyone is really shopping the resale market from Black Friday through the end of the year, so maybe next year, haha!
I don't really miss the items I sold - one tip I would give is to make a list of ALL handbags (I used Excel, and also added the keyfobs and scarves, etc. to the list). Then I just kept re-visiting the list, so I could critically see how many items I actually have and which ones I could live without. I highlighted the bags/items that I regretted buying, impulse purchases, or bags that I never use anymore/just don't like to carry. This made it easier to move the item down to the "want to sell" area of the spreadsheet. Then I thought about it some more before actually selling
I know it sounds analytical, but I work with numbers/spreadsheets for my job, and this method just made it easier for me. It also helped me not regret anything, because I felt I really pondered my list before impulsively selling my bags.