I'd like to give this a go.
Big update, so I'll put it in spoilers.
Neither was really put to good use though as Cyndaquil basically took out all of Sprout Tower and then Falkner as I picked up my first badge.
Bugsy was also pretty easy as Cyndaquil took down the first two and Gastly put Scyther to sleep before taking it out as well
Then made my way into Ilex and I got really lucky by finding a Beedrill in the first tree I tried to headbutt. I caught it and a Drowzee as I exited the forest.
After a bit of training we were ready to go take on Whitney. I tried the same strategy that worked against Bugsy, but Gastly kept missing with Hypnosis. Fortunately, Drowzee was my backup and eventually Miltank went to sleep and it was easy from there.
My journey continued as I made my way to Ecruteak. I picked up a Pidgeotto and a Magmar, replacing Bellsprout on my team. My original strategy for Morty was to use Cyndaquil and see how far I could get before switching to Gastly. But Cyndaquil ended up doing much better than expected and took down everyone himself.
I kept going and fished for a Tentacool to be my surfer.
Made my way to see Chuck who ended up being by far the hardest to beat so far. Poliwrath essentially took down my entire team until Tentacool was finally able to take it down.
Jasmine was very easy however, as Magmar soloed the entire battle.
So that's where I am now. I'm going to do a lot of training before moving on, and maybe drop a pokemon since I currently have 7 that I am switching between. Will update more soon!