When I was young I loved getting the latest of everything but that was partly because I didn't have to carry certain workflows or older tech along with me. It's the baggage that we accumulate is the problem.

Now I understand why plenty of old timers just leave the OS version on the MacBook that it came with. All you ever really need is the security patches.

Unless there is some specific new feature that you absolutely must need or some push factor, don't upgrade.

For me its every time I reinstalled my OS and didn't backup any of my chat convo logs. My wife still has them on all her old Macs, and her first Windows computer we met online through has some (not all) of our MSN convos still on it. I never thought about that unfortunately.