So I found myself with a lot of spare time this evening so I decided to progress through my challenge.
Got through mount moon with minimal effort. Peck and Double Kick on Nidoran with Rock Throw on Geodude made everything you find in there a breeze.
Get to Cerulean City do the nugget bridge and head to Bills crushing each trainer that dares stand in my way. Help Bill out and head back to the city.
Decided to try Misty since my Nidoran is now Nidorino and lvl 24.
Got whipped by Starmie.
Decided to head to Vermillion to get more training.
Destroy all the trainers before Vermillion with ease.
Get my Diglett from Diglett cave.
Clear out the S.S.Anne and get ready to beat surge.
Geodude and Diglett both evolve.
Realize I need the Cascade badge to use cut so back to Cerulean I go.
Defeat Misty by using Focus Energy and spamming Horn Attack with Nidorino.
Head back to Vermillion and destroy Surge.
Train some more on trainers to the right of Vermillion.
Currently headed through Diglett cave to get Flash and then it's on to Rock Tunnel
Current team:
Giovanni Lax Lvl 29
Horn Attack
Peck
Focus Energy
Double Kick
Balboa Serious Lvl 27
Rock Throw
Magnitude
Self-Destruct
Defense Curl
Simon Sassy Lvl 26
Magnitude
Cut
Dig
Fury Swipes