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Did anyone ever answer this question for you? I've got the same issue.
One solution might be creating a mapkey that goes through the "Tools, Server Manager" picks and does the entries in the "register new server" interface.
I did something similar with a trail file tacked on to a custom startup for Pro/E used in our conference rooms. Had to have it so the local Windchill cache folder was wiped out after every session, but not require the user to go through the whole server registration process (possibly typing something wrong) whenever they used Pro/E as part of a design review meeting. This way the Pro/E (errr...Creo) session is right at the Windchill login step of registering the server and they connect to their workspaces as they exist on the server.
You may be able to get what you want by having a custom Pro/E startup .bat file check the system for the Windchill cache folder. If the cache does not exist execute the trail file to establish a connection to the server, if it does exist have the .bat file skip that function and just call Pro/E without the trail file.
(I'm making the assumption you're connecting to PDMLink with Pro/E / Creo, but a similar approach should be doable with other applications with macros or custom batch files)
Erik
Please make an idea for this so it can be voted up.