Hi. I can't claim to be an expert but I'll like to help you figure this out if you don't mind. I can help on the Microsoft side of things as I'm a certified Systems Engineer and Systems Admin, so I'd like to get a better understanding from you as to what you're encountering with the server 2008 installation and vmware. Also, I'm curious as to your reason for choosing vmware as opposed to Microsoft's native solution, Hyper-V, which is already included with your server OS.
It's not about the money for me by the way, I'll like to try to help. If I can help you work it out then you can award the job and pay me what you're comfortable with. Also, I believe when setting up a project, you can choose a custom tier and enter your price range, or in your case, the next tier is $30-$250. If you wish, I'm open to communicate by skype or email as well.
If you have a moment, take a look at my profile/feedback as well. I have a high reputation for being efficient and providing excellent communication, so you know you're getting a hard-working freelancer. Kind Regards, Kenny.