Update #2!
I cleared Mt. Moon with 2 Pikachus, a Charmeleon, a Geodude, and a Mankey. All were level 20 except for Mankey, which was level 16.
First step into Cerulean!
After healing my Pokemon and stocking up for the gym battle, I headed straight towards Misty.
After pounding the lackeys with Shocker, I was ready to face Misty.
... Or so I thought. She pounded my team down into the ground that I raged and reset my game. :p So, I beat my way through the Nugget Bridge, and headed towards Bill's house. Oh and I caught an Oddish along the way.
After getting everything done up north, I decided to try my luck against Misty's Starmie. After one more rage and a use of a different strategy, I finally won!
Now, it's onto Lt. Surge. Geodude and I will get through this with ease... Hopefully...
Wish us luck!
(if this gets merged into a large post, I totally understand, as this might be considered double posting)
Update #3!
So I just set foot into Vermillion, eagerly hoping to fight Surge.
After training for a bunch by beating trainers and Pokemon to the east (as well as catch a Diglett named Diggy), I set myself to board the SS Anne.
While fighting through the whole ship (and healing now and then), I head to the captain's cabin. And who else shows up?
(not so good, thanks for asking)
After a quick fight, I proceed to enter the captain's cabin... Only to find him upchucking due to sea sickness. After a few pats on the back, I receive an HM covered in what I hope is just green water. Once teaching the new HM (Cut) to my Meowth, I set to fight against Surge.
After beating every lackey there, I must now get through the gates.
After many tries of trying to find the got-dang switches in the trash cans, I now face Surge.
Aaaand, Graveler and Diggy beat up his team XD
Now, onto Lavender and Celadon!
(probably put those two together for a large post)
EDIT: I'll probably just do one more update, most likely the Elite Four and Championship.