I just verified. You can install Python 2.7 on an up to date Windows install as well as an up to date Linux install. Python 2.7 hasn't received security updates (or really any updates) in years, but that does not mean it can't still work on an up to date OS.
Yeah, it's been 5 years (almost 6) since python 2.7 stopped receiving security updates, but it does still run on modern OS's.
Looking at the list, I'm actually kind of surprised there aren't more CVEs for python 2.7, but if you're only running it locally or on an intranet I could see letting it ride.
Nothing like a full rewrite. I migrated multiple projects, but while there is a significant amount of work involved its a tiny fraction of what a full rewrite would require.
Did it a couple of times. Not something you can do with your eyes closed, but not even close to the nightmare of upgrading a JS application or upgrading a rails app.