Tom,
I'm up and down the coast with some regularity, let me know if you want me to make the drive out to the coast sometime.
For VMs, I would recommend a Linux host, then the only OSs you have to buy are the guest OSs. Not sure about your version of Medware, but yes you can easily use a desktop OS for Quickbooks, and probably for Medware.
That way the only server OS you need is for AC (and the domain controller, AD, etc)
It makes reverting a upgrade that goes bad as easily as copying back a cop of the VM. It also makes evaluating new software or upgrades far easier.
Linux as a host is about 1-3% load, so effectively transparent. There are also binary pass-through drivers for Windows now.
