Well, I am not worried about trivial questions which can be easy to google. The problem I see is two-fold:
First, the lack of tutorials/videos on relevant topics that are up to date. For example, the Django with PyCharm video didn't have any audio and, last time I looked has not been replaced. I find video presentations to be particularly efficient as a means to quickly communicate intended usage and workflow.
Second, support becomes invaluable when it comes to non-trivial situations. For example, I still don't have an answer for this:
https://news.ycombinator.com/item?id=8569766
I frankly didn't even try to reach out to support due to my prior experience. And that's the issue. I have no problem with paying for good product. And I want to stress that PyCharm is a damn good product. When I do there's an expectation of quality support.
So I find myself at a strange point. I would unequivocally recommend PyCharm to anyone considering it. It is a very good product. And I have to do this while not being thrilled about their support, which feels really weird.