Technical debt is better managed through gradual refactoring as part of the normal development processes. Of course there's still going to be a struggle between taking time to maintain code quality and sales wanting the next feature yesterday, but it's a different argument than "we want to rewrite this in shiny new framework X because someone on Hacker News said so" (not that this exact argument will be used, of course).

Automation I'd see more as a sensible move, if it reduces costs in the long term. Again it may take a back seat to short term priorities, particularly when cash is short.