zlacker

It depends on your philosophy and your server setup. While my agency/host is proactive, most of my clients were running 7.4 up until a few months ago. 8.o was released two years ago, so you could argue we were/are already employing this strategy.

Eventually you have to upgrade. Do you want to go from 5.6 to 8.2 and possibly have to start over? Or do you want to go version by version, paying smaller amounts more frequently to stay current?

Also: WordPress + Themes + Plugins works best when you don't delay maintenance/upgrades. Everything needs to work in concert. You might be able to freeze your theme in time, but your plugins and the WP core will march on.