@ned Weird, I was just talking about this with my brother in law last week, similar situation, wondering what Pokemon to start the boy on. For us, we wanted to keep it to the original 150 (to keep it simple), but the original Gen 1 games have outdated type rules (for super effective stuff) so it might be confusing. We ended up deciding on Leaf Green or Fire Red which are basically remakes of the original games with the modern type rules and features. Undecided if we go PC EMU or handheld.