Leaving aside the bugfixes they've kept publishing for Python 2.7 (and it's rather massive standard library), how is your stack of ~100 external dependencies holding up? In my experience, most libraries are dropping Python 2 support too. Many dropped it a while ago.
Your locally running, toy projects will continue to run under Python 2 indefinitely. Large [esp network-facing] projects will start to fall apart.
Many large Python 2 projects come from age when it was not exactly practical to have ~100 external dependencies and thus do not have that. It was the time when one really though about whether having external dependency for this particular shiny thing is worth the deployment hassle involved.
Indeed. The main project I work on at the day gig is old enough that it's build on an in-house framework that predates the first public release of Django.
Your locally running, toy projects will continue to run under Python 2 indefinitely. Large [esp network-facing] projects will start to fall apart.