It might* go ok. Personally I would strongly recomend a clean room install, it is far less likely to cause unusual and difficult to pin down issues later on.
*In the same sense that an upgrade of windows 98-2000 might go ok.
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.
There were a few exceptions going from 3.5 to a Boing Bagless 3.9 though, but those were easy to pin down and the 3rd party docs are readily accessible explaining what to do (usually ended up keeping some of the older files).
It's always wise to seek out the latest versions of the important OS software though. Searching Aminet or
the net yields great results.
