Getting a remote user to join domain

I have a remote user that at the time I built his Vista 32 Business
laptop did not need to part of the domain as he was rarely if ever going
to be on our local LAN. Everything was installed with the laptop being
in a workgroup instead of domain.

Now we are using Microsoft Dynamics CRM 4.0 which from what I can tell
requires machines to be part of the domain.

We have a Cisco ASA 5510 which we he can successfully VPN connect to.

Logged on locally and the VPN established I can change from a workgroup
to our domain. Am told successfully joined the domain and to reboot.

Here is the conundrum. After rebooting because we have yet to login
the VPN hasn't been established so if we try to login to domain\username
is told that no servers can be found. I can logon locally but when I
try to configure CRM it fails because I'm not logged into the domain.

How can I get a VPN established before boot up or before logging in?
How do I get all his "stuff" programs, files, settings moved from his
local profile to his domain profile, or do I just have to suck it up set
everything up?

Thanks in advance
John


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Kearsarge