He's right to a certain point. You don't want to upgrade needlessly until you have to. Example is a new feature improves business productivity or the software developer no longer supports your current platform (like Windows XP is no longer supported by MS). When a software company no longer supports your current platform, new found vulnerabilitie s may go unpatched and may compromise your system or data, resulting in a cost that is higher than upgrading to begin with. In that case, it makes sense to upgrade.
Copying any licensed software is stealing. If you want encryption software, there's plenty of freebies or opensource software out there that would do pretty much the same. I use VeraCrypt for creating encrypted volumes, etc. It works great.