To decide on Oliver or Winston, we need a best out of five.
On the first round, Oliver won with voting 11-10.
But now, we need to see who Magic 8 Ball things would be best with me.
Now let's ask the questions!

Q: Is Winston + Flec the best ship?
A: Most likely

Q: Is Winston + Calliope the best ship?
A: Yes, definitely

Q: Is Winston + Cal the best ship?
A: Concentrate and ask again.

Q: Is Winston + Coco the best ship?
A: You may rely on it.

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Q: Is Oliver + Flec the best ship?
A: Yes

Q: Is Oliver + Calliope the best ship?
A: Outlook good.

Q: Is Oliver + Cal the best ship?
A: Better not tell you now

Q: Is Oliver + Coco the best ship?
A: My sources say no.

SO THE OVERALL TALLY IS: WINSTON: 3, OLIVER: 2
Which makes the winner of the second round. . . .

WINSTON!!!