Hi, I've been a developer for more than 7 years building high traffic web based application from scratch with asp.net , C#, and SQL, and I've work with different industries.
Your sub-domain configuration codes are simply a few lines of code to detect which requesting URL and maps the path to images and other physical files appropriately (no need to maintain this).
The sub-domain forwarding can be setup in a couple of minutes in IIS such as adding header like this: subdomain.YourDomainName.com. You can configure the IP address to route to either the same server or different server (a copy of your app is deployed by simply copy and paste).
I run a small IT shop specializing in web based (.NET) application and can build a quick prototype of the website and demo it to you in a week with no charge.
The app will be built with at least 70-80% of the listed features on the suggested website. Other features, you may not need them at the moment.
We provide daily report with milestone demo as well as QA & automation testing to ensure the application is bug free.