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Masem
Elements of Harmony - Had an OC in the 2022 Community Collab
Twinkling Balloon - Took part in the 2021 community collab.
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Fine Arts - Two hundred uploads with a score of over a hundred (Safe/Suggestive)
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Helpful Owl - Drew someone's OC for the 2018 Community Collab
A Really Hyper Artist - 500+ images under their artist tag
A Really Classy Artist - 250+ images under their artist tag
An Artist Who Rocks - 100+ images under their artist tag

@WinterCutieMark  
Only of the same card, 3 at most - at this point I think there are now 4 different Dr. Whooves cards (Unblinking, Just In Time, Too Splashy, and Experienced), so you can theorhetically boost one to +11 by the end game. Alternatively, you could have all 3 of this one in play each with +9.