Take a look at the commit history for upstream (Google) gyp: https://chromium.googlesource.com/external/gyp/+log/refs/heads/master
As I am writing this, upstream gyp has updates as recently as the 12th of May 2020. These might fix bugs that we are still affected by. (I don't think the NodeJS or node-gyp copies of gyp have been synced with upstream (Google) gyp in quite some time, right? Maybe as long ago as 2015?)
Unexpectedly to me, there are many Python 3-related patches landed there in 2018, 2019 and 2020. About half of the commits in those years are Python 3 related. But there are other fixes as well.
Perhaps these are redundant to changes here, but perhaps not. I think it would be worthwhile seeing what has changed there, and if we could benefit from those things here/in the NodeJS world.