@IrieMangaStudios
 
That is some very sound logic. XD I’m wondering if which characters you’ll introduce for the other straw hat crew roles, given we’re out of mane six characters.

I hope this continues. ;3;

@sigh  
Not the hat!

I found Fluttershy-Spike and Chopper-Usopp pretty much interchangeable but to me and the artwork I draw, Shy and Chopper match personality-wise more outside the physical-character traits when matched up with Spike and Usopp.
 
Heck, when Spike had issues with his contributions to the Mane 6 (as Humdrum), it echoes how Usopp was during the Water 7 arc.
 
Some folks rather go with Spike-Chopper due to being the odd creature out dragon with ponies, reindeer with humans. But their social stature interacting with the majority is pretty different, Spike does not have the social anxiety in social interaction like FS and Chopper has.
 
Usopp and Fluttershy are cowardly (spike and chopper are not exactly brave either) but their approaches to stress are handled differently as well. It really seems out of character for Shy to boast or lie as well as Usopp. Spike seems more in showmanship or carry a presentation like Usopp does. Shy and Chopper are both very bashful when praise and attention is placed on them.
 
Also to take account of end goals, Usopp wants to be a great Warrior of the Sea, Chopper wishes to be a Doctor capable of curing any aliements, Fluttershy is a caretaker of animals and look after sick creatures, Spike has daydreams of being a knight or hero and has the potential of being a great dragon. Spike and Usopp’s goals seem in line with each other on being better than they are currently while Chopper and Fluttershy’s goal seem closer together.
 
Those things I try to piece together when matching up. They are not really the same character but it doesn’t mean they are not interchangeable.

@Background Pony #2D8B  
You can ship Fluttershy with Chopper, but conflating the two personalities is probably going to be a weaker comparison than any alternatives.

@Background Pony #2D8B  
Rarity is Nami  
Applejack is Sanji because she cooks, she kicks and she will end you if you mess with her friends or wasted food.  
Fluttershy is… Usopp? Meek, weak but resourceful and courageous when the going gets tough.  
Spike is Chopper.

Twilight is a great choice for Nico Robin. Now give us Fluttershy as Chopper and all will be right with the world.

You changed the hat you bastards! Nobody changes the hat!