Checking chain wear is low drama maintenance that prevents expensive follow-on problems.
Keep the routine simple
If you ride a lot in bad weather or on gritty roads, check the chain regularly with a wear indicator or during cleaning. You do not need to obsess over every ride, but you do want a repeatable habit.
What you are trying to avoid
An over-worn chain stops matching the rest of the drivetrain cleanly. That is when a cheap consumable turns into a cassette bill.
Good local shop help matters
If you do not want to measure this yourself, a shop with a strong service reputation can fold it into a seasonal maintenance check.