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I believe corporate red tape one of reasons to not-pay for a software licence. If you download the trial or non commercial edition, works for you, you would never go through chain of approvals to buy a cheap software.Meare player is an example that you can think of. Araxis merge, Visual studio, Visio are some to name a few.

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Depends on where you work. I've been in shops where developers had a certain amount of money -- $500 or $1000 -- to buy whatever work-related tools they deemed to be helpful in getting their jobs done. Those tools could be software (Beyond Compare and ReSharper being popular ones) or hardware (monitors!) and up to that amount there were essentially no questions asked (the only caveat being if you spent on stuff that was not needed you risked ruining it for everyone else so you ran the risk of a getting a Code Red from the dev team if you wanted to spend wastefully). As much as companies spend on finding and keeping good developers, dropping $1k/each per year for things that make them happy is chump change.

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