I noticed the warning sign for such accumulated crust and culture, is usually a exponential dev team growth curve.
We just need 4 new devs this year and 8 new devs next year.
All that while the actual product is at linear growth.
Yes, it works, but its foreseeable that it will end working in n-years were dev-team size and cost is bigger then the whole money the product earned.
A warning sign isn't actionable perse though. All of our developers know that we're heading for a disaster, be it in a decade or 2 years. But given that we're busy a 100% of the time implementing new features for existing customers or setting up our software for new ones. There's no time for us to start fixing this mess, and even if we did: that doesn't pay the bills.