Visual Studio 2008 - Unable to start debugging on the web server

I'm receiving the following error message when attempting to use the local IIS web server to debug my web application:

Unable to start debugging on the web server. The object identifier does not represent a valid object. (Exception from HRESULT: 0x800710D8)

I stumbled on this blog post which details this exact issue. I verified my log files in IIS and what I found is as stated in the blog.

#Software: Microsoft Internet Information Services 7.5

#Version: 1.0

#Date: 2017-10-17 20:14:47

#Fields: date time s-ip cs-method cs-uri-stem cs-uri-query s-port cs-username c-ip cs(User-Agent) sc-status sc-substatus sc-win32-status time-taken 2017-10-17 20:14:47

172.30.21.72 DEBUG /enrolment/Login.aspx - 80 - 172.30.21.72 - 401 0 0 372

I've also ensure that I'm running Visual Studio 2008 as an Administrator and that I'm using an account that is in the built-in Administrators group, as Microsoft explicitly states these as requirements.

I tried clicking the "Create Virtual Directory" button in Visual Studio after entering an already existing domain (which I added as an entry to the hosts file) which in turn creates a Virtual Directory/Application in IIS, just as it should.

I also tried resetting IIS using the iisreset.exe command several times throughout my changes.

All in all after hours of searching and playing around with these settings I still can't seem to make any headway. Can somebody please give input on what they would attempt next.