I am genuinely surprised at how much others spend on software. I started totaling up his list (excluding monthly services like dropbox) and stopped when I reached $500, which was right around Cornerstone.
For example, unlike Windows, there is no free and convenient svn utility on the Mac. If I were using svn on the Mac frequently, Cornerstone (which is quite expensive by my standards) would be a necessity.
Twenty years ago, computers cost $5000 and $500 worth of software was no big deal. Well today, that $500 dollars will buy you just a much a productivity boost, so why is it no longer worth it? Don't compare the $500 to the price of your computer; compare it to your already-spent salary plus overhead.
In my view, most of us who love free software have a knee-jerk reaction to paying money for software. Try spending a little more per year on software and observe whether or not it improves you life. It did for me.