Is there any chance this list might work?

I've been toying with the idea of keeping enemy ships ionised and slowly killing them with Oicunn's ability.

Captain Oicunn — VT-49 Decimator 42

Expert Handling 2

Extra Munitions 2

Emperor Palpatine 8

Intelligence Agent 1

Ion Bombs 2

Ion Projector 2

Ship Total: 59

"Deathrain" — TIE Punisher 26

Enhanced Scopes 1

Extra Munitions 2

Cluster Mines 4

Conner Net 4

Experimental Interface 3

Ship Total: 40

I think your build doesn't really play to the strengths of either ship. Bombs on a Punisher? The other guy does that better. Deathrain really kicks with Fire Control System. You have cluster missiles, make the most of them.

I think for all the points you have on your Decimator, you should probably break off 5 for Gunner. It's my understanding that you'd want Daredevil instead of Expert Handling, as you can overlap and trigger your pilot ability with Daredevil. I think if you want to run the Emperor you would need a third ship to make the most of his cost. Good luck, and test it as is. You never know until you fly.

Well, Daredevil is the typical choice for Oicunn, because of the double bump. But I'd argue, that Expert Handling probably works better with the Ion Projector + Palpatine + Intelligence Agent combo. Your primary concern is making your opponent bump into you and with a Barrel Roll, you can cover a bigger area. Additionally, you don't damage yourself.

That said, depending on your opponent, Daredevil might still be the superior choice. You'd need to sit 3-5 rounds in one place even for a smaller ship in order to destroy it with Oicunn's ability. Against a list with more than 3 ships, I'd be very surprised, if your opponent doesn't manage to destroy Oicunn during that time window.