I have a 2019 MBP that still has MacOS Catalina installed (10.15.7). Until recently, this has suited me fine. But now, one of my 3rd party apps (Adobe Lightroom) has discontinued updates & upgrades for Catalina. I'm not ready to buy a new MBP, and in all other respects I am still happy with my 2019 MBP & Catalina.
As you know, the Software Update
app offers only an upgrade to the latest version of MacOS; now MacOS Ventura. I feel that an automated upgrade of three versions may be riskier than a single-version upgrade, but I have no real basis for that conclusion.
Beyond the Adobe Lightroom app, other 3rd party apps that I use frequently are BBEdit, MacPorts, Launch Control and Microsoft Office. I assume that all of these apps will require re-installation following an OS upgrade. This looks to be a rather time-consuming effort, and so the prospect of repeating this upgrade procedure 2 or 3 times is not particularly appealing.
And so that's my question: Am I less likely to run afoul of entanglements by adopting a "single-version-upgrade-at-a-time" approach, or does a "multi-version-upgrade" impose an insufficiently smaller risk to warrant the additional time & effort?
One other item: I maintain current Time Machine backups. It is my plan to make a final update to the Time Machine backup for Catalina before embarking on either upgrade path. Is it safe to assume this would be sufficient to allow me to "back out" of either upgrade process, and restore my system to its current Catalina state?
"Time machine - yes - but do not update it so you can use it in Catalina."
Sorry, but you've lost me on this comment. Are you referring to the fact that TimeMachine for Catalina was the last version to use HFS+?