Hmmm... maybe we should anticipate the future Earth-Moon configuration, and go to a 50-day month right now. Each year is 7 months long, with 15 holidays - say, two between each pair of months, with an extra one thrown in at solstice time.

The months could be ten weeks of five days each. Three working days and two weekend days?

I'm starting to like this a lot!

I don't know where I ran across this, but...
I remember that when I was a kid I learned your out-then-back-in projection for tidal evolution, but I've recently read (wish I remembered where) that it's no longer expected to work that way. Possibly because it takes so long for the outbound leg that the sun does its red giant bit in the meantime, which seems likely to throw a monkey wrench into the whole scenario... but I don't know if that's the right explanation.