Yay a contest! I myself have already voted, so I am done with the voting. Welcome Cosmotone8!
I think starters would be best but it is more simpler to draw than things like legendaries as Olli already stated. Although if we did do legendaries it would be more complex and detailed to draw. I really don't know about the Best of blank region although it does sound interesting. Anyway here is how I kind of view it :
Legendaries : Intermediate/Hard (depending on your choice)
Starters: Easy/Intermediate (depending on your choice)
Best of blank Region : Varying
Also I have a question : Can we draw more than one pokemon, when the competition begins? :D