Hi Dan, I’ recommend giving the docs a good read to start. Here’s the start of the section on server.json
https://ortus.gitbooks.io/commandbox-documentation/content/embedded_server/serverJSON/serverjson.html
And here’s the page speific to aliases:
https://ortus.gitbooks.io/commandbox-documentation/content/embedded_server/aliases.html
And to answer your questions categorically;
> THis includes a servers.json file…i don’t think this is the file I need to use to update for virtual directories.
nope, you can ignore that servers.json file. It’s an internal file used by CommandBox to keep track of all the servers you’ve started in the past and what settings you started them with. It’s used for commands like “server info” but you should never need to touch it yourself.
> So, when the docs say webRoot for server.json, is that my path say c:\inetpub\wwwroot\testApp
By default it’s the web root of your server. So if that path above is the web root, then yes that’s where the server.json would go. The first time you start a server and specify at least one parameter to the start command, we’ll create the server.json file automatically for you. Note you can have as many servers in as many directories as you like and they can each have their own server.json fie.
> what is the servers.json file in .CommandBox and is it different from server.json?
The servers.json in the CommandBox home is an internal file to track the servers you have. Ignore that file. The optional server.json in your web root is used to default settings for that server and will automatically get picked up when you run the “start” command.
> So now, i want to create virtual directory mapping like i use in IIS…how and where do i do this?
Read the docs above 
> I think it is an alias, but I am not sure how to create it, and then get the server to read it.
Yep, we call them aliases (like Apache and Tomcat do). Create the config in your server.json and it will get picked up the next time you start the server
Thanks!
~Brad
ColdBox/CommandBox Developer Advocate
Ortus Solutions, Corp
E-mail: brad@coldbox.org
ColdBox Platform: http://www.coldbox.org
Blog: http://www.codersrevolution.com