When it comes to the deep web i.e. corporate applications, business tools etc, it's just not seen at all. These are the things that produce a lot of value and solve a lot of problems. I'd argue they are cumulatively more valuable than the above.
EsEnt, AppFabric, IIS7 ARR, PowerShell cover your concerns above all of which are scriptable and automatable.
When you consolidate your time across the year spent on developing a backup methodology for your server, managing updates etc, monitoring, testing, where does that leave you? I know Linux inside out (I've been a professional user on and off since 1998) and I know you hit the same number of roadblocks as windows along the way.
Also your deployment model sounds odd. Do you check in your production artifacts/dlls and configuration? Do you build on your production boxes? Also your demonstration applications are tiny. A single deployment we throw out has 95Mb of release compiled DLLs across 48 assemblies...
We use NHibernate and have a test harness for MySQL already so we're not bothered about SQL pricing (anyway it's still plenty affordable as our product is valuable and pays for the licensing).
I was using rsync on Windows 2000 back in 2002 to sync press image libraries so that's a moot point really.
Azure cuts it for the ramp up phase of your product if you factor in the above. We did a proper cost analysis.