I usually run on a 2 year cycle where I work, unless there are some really important updates then I'll upgrade every year. Though it should be said that I'm working for a firm, so I'm not responsible for my license costs.
Depending on which version you are on, making an upgrade may be super beneficial. For us, since we use a lot of scripts, getting this upgrade for Max went a long way as now we don't have to push scripts to users anymore and we can just store them on a network drive. https://cganimator.com/how-to-manage-tools-part-2-plugins-featuring-new-pipeline-integration/
Max 2023's retopology tools are also quite useful if you need to quickly remesh a client supplied or downloaded model. If you don't have a version of Max that supports open subdiv, that can also be a useful tool over turbosmooth for getting nice creases in furniture models.
But in the end, if your business is thriving and your clients are happy then do you really need to upgrade? That's
