Jennc:
I am not going to try to diagnose the recommendations below but instead I will tell you how I do it. And I have been doing this since DNN version 1.0.x. and it has worked great for me. As you know, IIS in Win2K and XP only allows you to have one true Web Site, the Default Site. My method works within the confines of this limitation and taking advantage of DNN's ability to host many sites with one software installation and one Web Site in IIS 5 or 5.1.
First make sure that your installation works properly for Host. For my method to work you have to go to the IIS manager and change the Home Directory for the Default Site. Specify the physical directory where you installed DNN. In my case it is c:\inetpub\dnn441. After doing this run the IISReset command. By doing this you will be able to run your site locally by just specifying "localhost" as the URL (yes, no weird virtual directories). Test this please.
Now you are ready to login to your local site as Host and create more Parent Portals. The trick now is to be careful with the naming of the Portal Alias. Let's say you create a new portal and use the alias "testportal1.com". Then, go to the IIS Manager and edit the properties for the Default Site, in the "Web Site" tab, click on the Advanced button, then add testportal1.com as a Host Header for the site.
Then, (follow me here) open the file “C:\WINDOWS\system32\drivers\etc\hosts”. This file has no extension but it is a text file. Under the line that reads “127.0.0.1 localhost” create a new line that reads “127.0.0.1 testportal1.com”, make sure that when you save it the file remains without extension.
Run IISReset one more time just in case, I have seen things not work properly right away but they work just fine after rebooting IIS.
You should now be able to run your browser and enter “testportal1.com” and connect to your new Parent Portal.
See how this works and post any questions you may have. You can repeat the process for every new Parent Portal you wish to have. All of them should work fine side by side by just specifying the portal specific URL (alias/domain) for each, just like on a server
Carlos