I get asked that one a lot. If it’s been over 3 years, to me, that’s a yes. Mostly because Quickbooks won’t provide any support for versions that are over 3 years old. If you were to call for support, they won’t help you and will say that you need the latest version.
Additionally, loading older software onto newer machines may not provide past functionality. I recently did this and my ability to generate reports in pdf format didn’t work. Now I have to spend some time troubleshooting that one.
How often should I upgrade? That’s another popular one. My answer to that is every other year. Rarely does one years upgrade change that much in functionality that you would need to upgrade every year. Mostly what happens are bug fixes. If you keep up with the updates, you will get those anyway. So unless you have some critical process that needs to be fixed you can wait a year.