Do you headcannon the playable character as yourself?

Not really? Never thinks about it too hard, honestly. Cannot really recall any major choices in any Pokemon game. Railroads you down the same route. Never leads to the question of "what would you do?".

Extends to games with those kind of choices too, arguably. Picks based on feelings of what seems best for the situation. Remains separate from the character, however.
 
No. Every single time a game I play has a blank slate or customizable protagonist, I create an original character for that run. Pokemon's no exception.

I almost always give them a punny name relating to the theme of that run. If it's good enough for the Gen 1-6 Gym Leaders, it's good enough for me.
 
In the games where I can customize my character, I pretend it's me going on an adventure. In the other mainline games, it's a bit more detached. As for Colosseum and XD, I feel that Wes and Michael are their own characters with their own personalities.
 
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