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Pixel Perfection - Hot Pockets Spotted
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Twinkling Balloon - Took part in the 2021 community collab.
My Little Pony - 1992 Edition
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Wallet After Summer Sale -
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Not a Llama - Happy April Fools Day!
Magnificent Metadata Maniac - #1 Assistant

Pomegranates :P
Bummer that Jim didn’t answer the second question.  
My guess would be that it’s a small fishing village near Vanhoover or Tall Tale.  
The scenery does look vaguely Pacific Northwest.
thps48
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Wallet After Summer Sale -

Young Leosword
Seaward:
 
>>1262572p (merged)
 
The new map:
 

 
Let’s see, I don’t entirely recall, but I think Horse Washington, Horse Florida, and Horse England are all named something else. Which is what my choices would have been if that weren’t the case. Of course, random crap is constantly appearing on the map including Our Town, Yakyakistan, and the giant unknown stretch of land jutting out of Horse California. X3