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If the only way your organization can prioritize this is either “drop everything and update” or “completely ignore and do no work to prepare,” then it sounds like Python versioning is not your biggest problem.

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I get this, though: porting code affects all parts of the code base, so it generates git conflicts all the time. It's way more of a pain to do than routine feature development or refactors. It gets difficult to have part of the team work on features while another group works on the port to a new version, because that generates a ton of conflicts. It's easier to get the entire team working on the port.

I had to manage a mature codebase upgrading Ruby versions, and it was painful. And that is fairly mild by comparison; not the big jump from Python 2 to 3.

Unfortunately, I think this type of thing actually is the case for many organizations. Trying to explain the business case for paying off technical debt to a non-technical person can be very difficult when "right now everything works."

I've had to fight developers over this.

A lot of devs like to not worry about new things.

I can really understand that… but I believe that such organizations will experience significantly more problems than just Python upgrades. (I work for one.)

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