With the backing of a stronger bonfire I decided to return to Undead Berg to check on the doors I couldn't open before. I also tried fighting the red dragon again and just got roasted. Lol. I did find a path leading to "Lower Undead Berg" though, which I had completely missed before. It was populated mostly by hounds and assassin hollows who were at this point no match for me. It also had a hag who sold handy posion coated stuff!
This is one of the few games where you can literally buy shit.
After rescuing a novice mage named Griggs (apprentice of the Big Hat guy) and defeating a bigger twin weilding demon I found a door to the sewers which was inhabited by undead rats, yucky slimes, and cute, big-eyed frogs. I also rescued a pyromancer named Laurentius "of the great swamp" who had somehow gotten stuck in an urn. Towards the bottom of the whole place was a big arena, and unsurprisingly home to the resident boss critter the Gaping Dragon. Fortunately Solaire had also returned from Anor Londo and was present to assist!
Poking from the back: the "go to" method for most of these bosses.
While the dragon did thrash my ally who I suppose had to go back to a bonfire to recover, I got to see its very limited move set which rendered the rest of the fight very simple. Beyond him was a deep well leading to... Blighttown. Again? Since I hadn't been on this side yet I figured I'd clear it all the way down to the swamp. Those poison dart guys are annoying. Interestingly, once I got to the bottom, Shiva was no longer there. Ser Chubby was though, and was in dire need of anti-poison moss. Lucky for him I had a few spares.