Big upgrade on Mac

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For a long time I've been planning to upgrade the OS on my Mac. I'm currently using Mojave and can move to Ventura which is four steps I think. I've stuck with Mojave because it lets me use PS CS6. I'll lose a lot of stuff with an upgrade but I reckon I've found ways of dealing with it, mostly courtesy of Affinity, and a reasonable sized outlay of cash. I don't need the highest spec processing stuff but I am used to PS6 and Photolab 4 (which will also die).

I upgraded my wife's Mac a month ago, just one step, and the whole thing turned into a nightmare and in the end I had to erase the hard disk and reinstall from the back up I thankfully had. All in all it took the best part of 3 days before it was fixed and a lot of fear, stress and trembling. So, mainly, I'm filled with dread at the prospect and am still considering staying where I am.

Has anybody done this, either a big upgrade or to Ventura and what was your experience? Also is it worth it or should I stick with reliable but ageing Mojave? All information and opinions welcome.

Thanks, Jim.
Have you got a decent back up that you can return to if it all goes wrong (which it shouldn't).
I've got a bootable back up and Time Machine. I know it shouldn't go wrong and never has in the past but recent experience showed me different, and this is a biggish jump, hence my nervousness.
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