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Re:Upgrading GitHub from Rails 3.2 to 5.2 by sidlls on Friday September 28, 2018 @06:01PM (#18097417)
Yes, four FTE engineers taking 18 months to upgrade across two major versions indicates a massive problem, but not necessarily with Rails or Ruby. That's a cost of $1.5M give or take, just on the engineers, not including the opportunity cost in new feature development or paying other equally important tech debt.
Re:Upgrading GitHub from Rails 3.2 to 5.2 by mikemotherwell on Friday September 28, 2018 @09:29PM (#18098224)
$7 billion dollar company, $1.5M cost? $7 BILLION. Your order of magnitudes are waaaaayyyyy off.

This is the inverse of survivor bias, in that you are retroactively applying "best practice" at the wrong scale. What gets you from $0 to $7B may hurt you at $7B. Heck, may hurt you way earlier than that.

However, and YMMV on what problem you want to solve, but saving $1.5M, heck lets 10X it and call it $15M, saving $15M when worth $7B isn't the problem I'd personally be concerned with.