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You might consider ubercart, it integrates well with the Drupal CRM and is very well documented.
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Hmm, Office Professional 2007 is a memory hog. You might consider an Open Source CRM for your web platform. Drupal is a very good one with lots of modules available and it's very well documented. Lots of support within the Open Source Community, and expertise can be had at a very reasonable cost.
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Hands down, no doubt about it. Microsoft's Small Business BackOffice Server.
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If you're connecting to a terminal server, it won't matter that the client pc's are memebers of a specific Domain vs. being in a peer based Workgroup. When you're authenticated into the Terminal Server you're signed in with Domain Credentials, at which point you're working from 'Virtual' Connections. The only thing you