I feel rather happy right now, as I just got Homesite 5.5 to run under the latest CXOffice (3.0)!! I'm not sure if these steps are all necessary - but I'm going to list what I did, in case someone else wants to give it a shot. I'm running Redhat 9, with XD2 installed - just FYI.
Okay - so I wiped and re-installed my CXOffice to clean up a few issues, and figured I'd give a few of my other programs another go, to see if CXO 3.0 had made a difference or not. I ran the installer for Homesite 5.5 which ran fine until it gave me the following error:
"Failure accessing file: c:\Program Files\Common Files\Vbox\Licenses\Homesite_5_8C5D.lic"
I let the installer finish normally, and then went to my windows install, and copied that file, as well as the "HomeSite_5_8C5D.prf" (just for good measure) to the appropriate mirror directory in the CXOffice install directory (by default: /dotwine/fake_windows/Program Files/Common Files/Vbox/Licenses).
I then ran through the startup wizard (which is where everything used to fail before - wizard would run, but not save - so you'd end up endlessly hitting the startup wizard), and that seemed to complete happily as well.
I had to adjust the icon entry and adjust it from using the "homesite.lnk" file call, and call the Homesite5.exe file directly - but that was a simple fix.
There are still a list of things that don't work properly, such as file browsing via any means, the drop-down menus, etc (which I still find suprising, given the support for various versions of Dreamweaver), but we're definitely on the right track!
All in all, I believe that Homesite 5.5 now can be moved to at least an honorable mention (if not a Bronze Medal) - it definitely does run :) Screenshot forthcoming...