3.7 (or maybe even 3.8) support will start as soon as we can have a "final" 3.6 - which might be couple months from now. I think 3.7 won't be done in 2019, unless some magic source of funding pops up.
3.7 it's a minor update from 3.6, that basically consists in changes to the standard library rather than the language, and 3.8 I think it will be the same, so once the 3.6 support is implemented it will take less time to implement 3.7 support.
Dataclasses are a sweet feature that I can see getting wide adoption pretty quickly. This said, they have a backport and it's mostly just sugar, so I expect one could probably get them working on 3.6 pypy.
The main way big corpos are sponsoring os is hiring the developers typically. That comes with a whole lot of things that some people don't want to deal with, like changing your place of residence
How realistic is it for an experienced programmer to dedicate 4 hours a week and join as a contributor? Not sure it is enough to bootstrap enough "project" domain experience to be productive. Asking for a friend.
There are some “easy” tasks to achieve 3.6 full compatibility, tell your friend to try it and see. We are around on #pypy on IRC, mostly european timezones
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https://blog.pyston.org/2017/01/31/pyston-0-6-1-released-and...
https://opensource.googleblog.com/2017/01/grumpy-go-running-...
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