As I recall, the primary reason I started using Linux back in 1995 was the plethora of free tools it offered. Say you enjoy coding avocationally or you want to learn a new language via self-study. If you’re on a Windows platform, you pay. For everything. Circa 1995, that translated to at least $100 per language (Borland C++, Visual Basic, whatever.)
Have fun finding a cheap FORTRAN compiler in a store near you; don’t even ask about Ada. (hey, everyone has their perversions…)
Compare that with dropping $30 for a Slackware CD set which provided gcc, p2c, f2c, and a whole host of other stuff. Sure, you had to become your own Linux sysadmin, but at the time that was a small price to pay for a very capable development environment. That path worked well for me but I had very specific goals, one of which was not to steal software.
I’ve been a professional sysadmin for almost ten years now and while I make it a point to use as much open source software as is practical at home and at work, I have no problem paying for commercial code provided it’s substantially better than what I can find for free. Three programs that pop to mind are Servers Alive for small-scale monitoring and alerting in Windows environments, and OmniGraffle and SuperDuper on OS X. I bought SuperDuper shortly after getting my MacBook Pro at work and have been backing up regularly - last Friday the ribbon cable between the keyboard/trackpad and the USB controller flaked out. My ass has been saved by $30 and some foresight (h/t to jwz on that one.)
That said, one of the problems that shows up in a corporate environment is when a vendor keys software to an email address. This is great for individuals, but sucks if someone in the Purchasing Department buys software for an employee. It doubly sucks when the person buying the software leaves the company.
This is not a problem restricted to the Windows world, though their model of pay-for-every-little-last-thing really exacerbates it. Red Hat’s entitlement system for their Enterprise Linux products was baffling to the point of being byzantine. Registration was a huge hassle and it took an act of Customer Service to sort out entitlements if for some reason you changed the IP address or name of your server.
In the intervening years the process has improved, but in the meantime I just switched our servers to CentOS and never looked back. I have no problem paying Red Hat for support, etc., but I can’t afford to not have patches just because of some stupid, broken licensing setup that I’m paying for!
Licensing and registration schemes are a sort of friction so if you want your software to have wide adoption in a sea of equivalent products, you need to reduce that friction to the greatest extent possible.