My Gangplank is Missing Something. Can you help?

I've been playing the Jolly Roger a lot lately, and while he still has a late-game surge, it's not quite there. Either my damage isn't super, or i get blown up super fast. I'm not sure if either is supposed to happen, but if you could offer insight, I'd appreciate it. A few things:

• It's this account so you can check this match history if you prefer.
• I'm running a Kelpto main tree and experimenting between Sorc and Resolve off specs.
• For Inspiration I take: Kelpto, Footware, Biscuit, and Cosmic Insight.
• I've also been leading off with Ancient Coin which doesn't seem to be doctrine but it really helps in terms of picking up lost gold, a mana bonus, and some extra warding. Unless there's a compelling reason to not do this, I really feel like it's a huge difference maker.
• To boot, between Klepto, Biscuit, Ancient Coin, and Oranges my sustain is ok.
• My barrels seem to be doing fine, damage wise. My Autos and Parley aren't (imo).
• Item build below to avoid weird spacing.

and lately to try to survive.