Python 2 to 3 (at least by 3.3 or so) was one of the easiest transitions I've ever done. There's a library ("six") to help, and in almost all cases you can write 2-and-3 compatible code, which means you can go piece-by-piece. (Unless your manager makes drive-by commits of py2-only code, months after you all agreed that all new code should be py3-compatible, and then leaves town for a multi-week vacation...) Dependenc…
Also, your screwdriver analogy makes no sense. The choice here is not about "your favorite tool brand". Mixing and matching tool brands is straightforward. The more appropriate analogy with screwdriver heads would be to imagine that you now need to change out all your hand tools, manufacturing lines, assembly robots, and equipment from multiple vendors from phillips to torx all at once. Sure, you can do some prep work, but you've got to coordinate a cutover at some point, in sync with tools that you have no control over or have to recreate from scratch. All for zero benefit in the end, other than the hope that they don't make the same mistake again with Python 4.