I'm betting NO on the latest dates, because they have the best odds.

The program is done. You don't recover from two consecutive failures.

There's a market that is directly about that, albeit with a deadline for an announcement this year.

How does this resolve if there's an uncrewed cargo flight to the ISS? Does that count as Starliner 1 or not?

I think the best approach, and most consistent with this market:
/EvanDaniel/will-there-be-another-starliner-fli

is to just go by the name of the mission. If NASA calls it Starliner-1, it's Starliner-1.

Will you close early if reliable sources say Starliner is cancelled?

Yes. Might wait a little bit to see what comes out of the mess, and wait for trading prices to settle in the relevant ways, but I expect that's a timeframe of days at most. If there are rumors of un-cancellation and the prices aren't stably near 0% I'd wait at least a bit.

If there is another Starliner test flight before Starliner-1, that would certainly make the 2025-03-31 date look unlikely.

/EvanDaniel/will-there-be-another-starliner-fli