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when is bitcoin useless?

If practically no one accepts it in exchange for something of value.

(1) Was I right about a bitcoin transaction in the jungle that gets broadcast later?

I suppose you could, but what's the point? Should the other party you exchange with also withhold completion?
Why does the exchange absolutely have to happen in the jungle?

(2) Just to be devil's advocate, can you think of a scenario where bitcoin is useless?

There are endless hypothetical scenarios. You just need to be motivated to convince yourself of them being realistic enough. Even if only to make a point.
And no, it's not just gold or fiat maxxis doing that. Bitcoiners do it all the time.