Chris, in response to your first question: do you already have a model open, when you initiate the File/Open dialog? The Revit Server icon does not show up in the left panel of the File/Open dialog, when you have a non-workshared file open.
Regarding your second question: an alternative is to run Revit Server between businesses via the Internet. Of course, it is not secure, but it eliminates the effort to set up and maintain the VPN. The only way someone could intercept the model, is if they tapped the line at the INITIAL instance of saving the model to Revit Server, or opening the model from a new accelerator. Otherwise, all subsequent activity is delta updates (what's changed in the model).
I am not endorsing this method. However, if you are already willing to use Revit Server on an unsupported platform, then routing via the Internet is adding marginal risk. So long as you have a dedicated 1 megabit connection with low latency, you should be fine. Just avoid having your home office connected via wireless to the Internet.