When should I use ACDSee Categories and when should I use keywords?
ACDSee Keywords can be easily written out to the corresponding IPTC field (but not for RAW or DNG, unfortunately). Categories cannot - or at least, there is no obvious plac to write out this information.
Therefore, the natural division would seem to be that Keywords should be thing you want to write out to the file, and Categories should be things you don't care about writing to the file. The main reason to write to the file as far as I am concerned is to make the information available outside of ACDSee. That might mean, making it available on another computer of yours, or making it available to other people, or transferring your whole catalog some day to another application. Anything that lives in Categories only is going to be harder to make visible outside of ACDSee.
The way I do it is, anything I think someone else someday might want to search on goes into Keywords. Things that I expect to only ever be of interest to me might be represented by Categories - but even then, I'm hedging, because if I ever want to migrate my catalog to another application, I'll want to find some way of preserving this. It would seem to me iView or any other application that supports any form of virtual organization scheme would have the same issue - how to preserve this should you migrate to another application. Temporarily writing this info out into a seldom-used IPTC field would probably be the way to go. But this seems just awkward enough that I try not to keep anything in Categories that I'd be *really* bummed to lose.
To my knowledge, there is no function within ACDSee to allow the writing of categories to keywords.
To some extent you can do this through Batch Set Information - you can assign the Keywords field (either the internal database Keywords or IPTC Keywords) to be the value of the internal database Categories. This doens't actually work that well if you category names have spaces in them - the individual words in the category names become distinct keywords. But this could also work as a means of exporting your cataloging from ACDSee to another application someday, if you first renamed your Categories appropriately.