Hi All:
I am faced with an interesting dilemma, and wanted to consult the oh'-wise-ones of this forum in hopes of finding the "right-way" 
Now onto my situation:
PREMISE: I recently took over a VMware GSX server environment hosting 6 guest OSes.
The Host OS: Gentoo with an Ubuntu 6.06TLS kernel
Guest OSes: Gentoo, Ubuntu and Windows
Host OS VMware Server version: 1.0.1
Guest OS Client Tools version: 1.0.1
Dilemma: After observing things carefully, I finally feel comfortable enough to "do something about this" where as, I need to upgrade all both OS and VMWare products.
Foreseen Issues/Possible Trouble:
a) the client's tools were all installed manually from source. No package management was used. As a result, I have a tar.gz in every single guest OS. How would I go about "uninstalling" such a mess, and instead using a proper package manager based on the OS flavor to install the latest greatest?
b) as mentioned in (a), the server was also "manually" installed. How would I go about upgrading the server to 1.0.5 without messing things up? Is it advisable to somehow uninstall/remove the server, and instead install the latest one via a package manager? Or... ?
c) what order shall I follow when attempting the upgrade pasth/task? A few friends advised me to:
-) Upgrade the Guest OSes with the latest patches then shut themdown succesfully.
-) Upgrade the host OS via a proper package manager.
-) Upgrade the VM Server software version.
-) Bring the Guest OSes back up and upgrade the client tools on each of them oneby one.
In the above scenario, you now know my hesitations... If anyone can offer an easier or better way of going about this, I will be eternally grateful. I look forward to everyone's contribution and thanks in advance
Sincerely,
-Russ
P.S. From what I understand GSX server morphed into the "free" server software, which is what we are currently using. VMware Server 1.0.1 ... That's why I'm using the GSX term. If I am using it incorrectly... my apologies! I am simply referring to the documentation found here: http://www.vmware.com/company/news/releases/server_beta.html