OK. The primary application that I need Windows for is Quickbooks Enterprise. I also still use my Windows Photoshop license since it was expensive, and not transferrable to OS X. My primary operating system is already OS X, and I only use Debian Stable on servers. I run Windows in a VM when I need those application, and only when I need those applications. How would you suggest replacing Quickbooks Enterprise? Do I just stop keeping accounting records? What about the 13 years of records that are already in the accounting system? Should I throw those out? What about inventory and accountant's copies? Will you train my customer's accounting firm to use some other package? What about the inventory database?
Microsoft has 90% desktop market share. Software developers won't support other operating systems until they have more market share, and people won't switch to other OS'es until there's more software.
If the software you need only runs on Windows then you should pay for Windows. Those that can move to Mac, Linux, etc and get away with using Wine or other alternatives should. The markets for alternative OS'es will grow then more people will be able to move.
Sounds like you are stuck on the Windows environment. You should stay and pay for Windows. There's nothing wrong with that.