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There are probably enough vtubers at this point that you could play "Who's that pokemon" but with vtubers.
>"Who's that pokemon?!"
>Is it Gura?
>"It's.... Mumei!"
Also Pokemon gen 1 romhack that replaces the pokemon with vtubers.
71 active. If you add the graduated one, surely this is doable with Hololive alone. But you can add the independent ones to spice things up.
How many pokemon are there in 1st gen if you don't count evolutions? Most have at least 1 evolution, so that would easily half the number of vtubers you'd need.
@alyx universal breeder 
@riserise
I did not consider that... breeding mechanic would definitely need to be considered. Calli & Kiara and Kronii & Mumei at the very least need to be compatible.
Ina'nis would probably replace Ditto. It probably has the most tako vibe out of all the pokemon.