a) we use one OU for our virtual desktops. we block inheritence so that we are 100% sure that only the settings we want are applied.
b) i dont think setting outlook cached mode for one user and then snapping would work b/c i believe that setting is specific to the mapi profile. you will need to create a mapi profile for each individual user. you may be able to get it to work, but i always try to defer to group policy whenver possible. in my experience it's just easier that way.
c) the issue we ran into with outlook 2007 and online mode was that using the instant search feature yielded inconsistent results. also when opening advanced find the filters were grayed out. we ended up having to install windows desktop search on the golden image so to alleviate our the search problems. we receieved many complaints about that during our initial rollout so hopefully this will save you the headache. if you do a google search for outlook 2007 advanced find you'll see what i'm talking about.
let me know if you have any further questios and please sure to mark this correct if it answers your questions.
cheers.