Honestly, the problem is documentation from the manufacturer. With the stuff I do at work, it's typically VERY detailed with what each revision has, or doesn't have. With these car companies, you get a brief description at best so you're not really sure what you'll gain....or worse lose.
Prime example is when HPT removed the ability to manipulate some emissions controls from their VCM Editor a while back. Now those settings are back, if you complete a training course, as has been pointed out here. Wait, but for years they were there without having to complete a course and they removed them without making it documented as far as I've seen. If you're savvy you keep a few revisions of their software so you can go back to a previous version when things like this happen.
Firmware can get a bit more tricky because it's the device software. Most want you to connect over the internet for the update and don't provide a way to downgrade after an update. What I worry about is letting the device update, and now all of a sudden my VCM Scanner or Editor version will no longer work with the new firmware (accidentally or on purpose) and now I'm forced to upgrade to a new version of scanner/editor that has features removed, or other un-documented and un-expected changes. If they offered the files for download and an "updater" where you could pick the version you wanted I'd not be as worried. You could keep several versions and go back to previous if something odd happens.
I haven't updated VCM Suite since 4.8.7 as a result of all this. Works fine on my car and I've not found I needed anything newer. Pro tuners have to update though as newer tables are added and newer cars need them.
You have to be careful as some will "auto update" when you connect them to a computer that has internet access. This is what Diablo did to me years ago that caused me all kinds of issues. I've also seen some HPT pro tuners have this happen and it wiped out their credit data and it required some phone calls to support to get sorted back out.