I always shot myself in the foot a little competitively, because I didn't base my favourite pokemon or the choices I made for my team based on which was best, or min/maxing, or whatever. I just chose what I thought looked best, or what I otherwise just liked the best (which is why Ditto still always maintains a spot on my team). So, my choices are:
1. Bulbasaur/Charmander
2. Chikorita
3. None - unfortunately, I just couldn't get into Gen 3, I really hope they re-make R/S/E for DSi or 3DS, though.
4. Chimchar
5. Snivy
I usually like the aesthetics of grass pokemon. Serperior is still one of my favourites, not just of the starter pokemon.