You would think so, but how much of your time is that $300 worth.

The way I look at it, Craft saves me so much time, the price is negligible compared to the extra work of a 'free' CMS. If you spend a few hours wrangling some crazy plugin on a 'free' CMS then you've already paid for Craft.

Free isn't always free, and $300 for what Craft does is a huge bargain.

Sure, if your time is worthless. When I can offer more value to my clients with less effort and in less time, that's worth an awful lot more than 300 measly dollars. Especially so on a $50k+ project... it's not unusual to spend 10 times that amount just in sourcing photo assets. Hell, I'll gladly pay a few hundred dollars out of pocket not to have to use Wordpress ever again.

Also, who wouldn't want great tools? You're a maker, aren't you? In another life I was a professional chef and was always on the lookout for the best tools to do my job. Not all tools are created equal: some are created with more care, last longer, have sharper edges, more comfortable handles, etc. I spent a small fortune on my kitchen tools because I enjoyed my craft that much more using them. How is this any different?