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Which is the point when you decide to go server less?

As early as possible. Things like AWS Lambda require you to really architecture for them in order to get the full benefit of it.

Lambda is also nearly costless if you have little traffic so it's not like you would pay extra for it. But serverless architecture isn't always the right decision.

Serverless shines when you have an unpredictable amount of async tasks to run, and those tasks can take a long time to run. Thumbnailing images for example.

Lambda has a 5 minute execution limit. It's not that great for background tasks unless you can divide them up to keep them comfortably under that limit. It shouldn't be that hard, but it's not effortless either.

Never is also a valid option.

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