If you think of it in terms of:
- how long does it take to get at new developer up to speed? (everything from readability to build systems)
- can this be hacked any day of the week if someone puts their mind to it? (both own code and libraries)
- can we be resonably sure that new changes don't introduce (large) defects? (testing, modularization)
it becomes impossible to argue that it cannot affect business success.
Yes:
- it might work as long as the old dev is happy and alive, but break down when he isn't available anymore
- it might work as long as nobody targets this business specifically
- it might work as it exist now but at some point be impossible to update anymore and the day new tax rules or whatever are introduced, it breaks
Still we were barely were scraping by.
We were forced to spend a lot of time to do tricks to make Windows 7 behave like Windows.
We couldn't take opportunities that showed up as the only ones who knew the software were SW engineers in another country, and they were unreliable.
We could have lived comfortably since our software was almost mandatory and we were the only supplier.
But we struggled badly and pay were late on multiple occasions and I was happy to leave after some years.