Part solution
Well, a part solution I have come up with is to mount the directory I want indexed via a network share and enable indexing of it like form the command line using the mdutil tool (mdutil -i on /Volumes/myshare)
I did this via a share because I have noticed that the normal mounted disks from Parallels are a bit slow, via the network it's much faster
This will probably not help you with Outlook, but it's a start. For Outlook you might want to try Google Desktop, I had(removed it, didn't like it) that at the office and it had an Outlook plugin