Advocating a particular position based on how you think your boss will react is the behavior of a sycophant and unprofessional. If you have a technical role, it’s your responsibility to advocate based on technical reasons. If you are highly uncertain, either do more research and experimentation or refrain from adding your opinion.

The premise is not having a strong technical position either way. It is advocating a consistent position - we should be effective at whatever we do next.

You'll notice that both scenarios involve a careful treatment of the risks involved, there is no point in looking for opportunities if the person responsible for choosing the level of risk tolerance doesn't want to tolerate the risk of looking. The only thing being modulated is enthusiasm for leaping into an uncertain situation.