The more people you have in a network, the more difficult your transition to a domain will be.
I would not recommend Windows Server 2008 for a small company. A system based on Small Business Server 2008 would be more appropriate. Its cost is comparable and it includes many features that are simply not available in standard server. This includes remote access features as well as Exchange Server for shared Calendars, Contacts, Tasks, and Email.
Domains provide many benefits:
- Centralized logins. With a workgroup
you have to define user accounts on
each system and to permit easy access
to the server, the accounts must be
identical as well as the passwords.
With a domain, you create one account
and it's used on all systems.
- Centralized Administration. You can
manage all workstations remotely as
well as the server with ease and
create policies to configure all
workstations at boot.
- Vastly improved security. Much easier group
management and assigning of
permissions to use.
- Software deployment. For example, create a
share, a Group Policy package, and
you can install office on all your
computers without ever having to
touch the machines.
And I'm probably forgetting others. For me, Domains provide easily configured networks that frankly, I rarely have to touch more than typical windows updates.