[fuhrysteve]

I find that it doesn't get too frustrating if you don't let it get out of hand.

Routinely prioritize keeping dependencies up to date, clearly depreciate "old" / bad code, and focus on coming up with good product designs that have reasonable compromises between time-to-market and high quality engineering.

You just can't let stuff slip. Don't let 6 months go by without at least trying to upgrade to the new version of whatever or without making some some progress moving from the "old way" to the "new way" for some component.