Macbook Pro macOS upgrade without losing applications (not owned under my Apple ID)
The update process deletes no application, so the update doesn’t make you lose anything. Upgrade processes can migrate known broken software to a new location, but there’s almost always a log file explaining what and why that happened.

However, you can’t roll back an update if an application breaks, so you might lose the ability of the program to use a license key, be supported, or even launch/run when your system changes.


Get a good Time Machine backup or other clone / backup so if your system breaks (whether you break it unintentionally with an update you apply, whether it breaks due to an update that self-applies or whether it breaks due to breakage, eventually all programs will stop running).
Think if you can reinstall the app if you erase your Mac, reinstall the older version / unpatched version in terms of time and hassle and knowledge.
Check with the vendor so you know your support options, both DIY / Free / Paid - this is key since the vendor can even kill your apps without an upgrade. In fact, Adobe just did this: 


https://appleinsider.com/articles/19/05/13/adobe-warning-of-legal-problems-if-users-keep-using-old-versions-of-creative-cloud-apps



In general, it’s safe to upgrade since Apple designs the system to not touch apps and settings, but even with that design, sometimes a bug ships and you get breakage for something that should have been easy and non-intrusive.