I suppose I should comment here since I suspect it was my theme Jeff was having a bit of trouble with in the Widget Map thread. Whether this is true or not, I think my experience with this issue might offer some insight. I'm always open to opinion on these type of things from others as well, which is one reason my Ideas forum is open for non-paying members.
There's definitely a fine line when offering a support-based service. On the one hand, you have many people that are getting a free theme/plugin and are expecting the support to be just as free. On the other, you have your paying customers, which you must cater to first.
While I consider my themes/plugins sufficiently enough documented to use "out of the box," I understand that's not true for everyone. Sometimes, as a theme/plugin developer, it's hard to figure out what Average Joe needs to get up and running. What's easy for one person might not be so easy for the next.
Personally, I'd like to offer the whole package for free, but that doesn't put food on the table. Now, this doesn't mean the theme/plugin itself will be "crippled," but it does mean that something has to be sold. If there were no paying users, the documentation wouldn't be nearly as good as it is now. I'd probably throw up three or four tutorials (instead of 30+ for one theme) because I'd either not have time or couldn't be bothered with it.
Essentially, paying users give me time to sit around and write the documentation they need.


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