Oh gosh... I wouldn't compare a WinBlows OS overlap upgrade to an Amiga 3.0<>3.1 upgrade et al. That's one of the beauties of the AmigaOS. I say he is just about 100% safe making the upgrade without doing a wipe and fresh install. Of course, if something goes wrong... lol Kidding aside, there really shouldn't.
I did and I'll continue to do so. Upgrading an established install is not a good idea, especially if you already have a large number of hacks/upgrades in that install. I will always recomend cleanroom installs for the simple reason is that it narrows down the list of possible foulups one is likely to face later.
And yes, I've had several AmigaOS upgrades puke on me, almost always due to stuff I'd installed to customise the system beforehand.
It's always wise to seek out the latest versions of the important OS software though. Searching Aminet or
the net yields great results.
Agreed.