Regarding specifically WP, which is how I made ends meet (and then more) for a number of years -- it's like crack, you hate it and you know you're better than this, but it's just makes life so easy if you don't resist. Not a perfect analogy, but what I'm trying to say is that, yes it's easy and you're fighting the uphill battle if you don't go with it. Plus, WP consulting can be very profitable, given how much of your code can be reused from project to project.

But, I have to say, at this time the flaws of WP are so well-known, and the direction and style of the WP devs are such a known quantity, that we as users/devs know what it is and we know exactly how good/bad it's going to be. It's never going to be a well-designed MVC application, and it's probably never going to conform to good OOP design either. It will probably continue to look pretty nice on the backend, but remain really annoying to extend for anyone but the greenest noobs. And it will probably have a ton of features which seem like bloat to people who simply want a blog, and like cruft to people who want a full-fledged CMS.

I think, after so many years, the cost of building a reusable system from scratch is starting to outweigh the benefit of just sticking with WP. One of the major pillars supporting WP's proliferation is the ease with which one can find hosting -- just upload your site, if it doesn't have push-button install already -- and I think the ease with which a Python or Ruby app can be deployed has now matched that. At least for a certain range of users.