What will the upgrade path from 4.2x be like to 5x?
Do you have to re-write your apps or is it upgradable?
From what I've seen 5.0 should be on par with the 4.x upgrades, which is to say, not bad. YMMV of course.
FWIW, the memory and instrumentation improvements in Ruby 2.x alone are worth the massive effort to upgrade. Good luck!
Getting stuck on 2.3 isn't desirable.
Everything else at the company is microservices now, but this one system still has a few million customers.
The question is whether they have the economics right to earn a nice profit; could be tricky, but I guess if you do it day in and day out you get it dialed in pretty well.
Looks like a fairly painless upgrade according to http://edgeguides.rubyonrails.org/upgrading_ruby_on_rails.ht...