What I find frustrating is when fans seem to care more about technicalities and legalities of obviously non-commercial fan projects.
I first registered for ENWorld almost 17 years ago, because I'd written an extensive and thorough conversion of the Dark*Matter setting from Alternity into d20 Modern. I'd converted just about every game-mechanical element from every Dark*Matter book, created/adapted character classes to fit the setting, and had sunk hundreds of hours over months of work into making that project.
I had been using it in my home d20 Modern game and my players had loved it. ENWorld at the time (don't know if it still does) had a library section devoted to fan conversions of older-edition materials to 3e and d20 Modern (as the current editions of the time).
I downloaded the template that ENWorld had for posting conversions, entered everything into the templates and framework provided, and put it up, hoping for feedback about my conversion efforts, and hopefully some appreciation of my hard work.
Instead the thread about it being posted was pretty much entirely people nitpicking the legal details of the project, and it was genuinely disheartening and discouraging because nobody even commented on the quality of the conversion itself. . .they only cared to talk about legal technicalities of the project.
A "hey, this is good work, I really like it, but for it to be legal to post here you need to change this and this and reword this" would have been a lot better welcome to the site rather than a snapping critique of the legalities with no feedback on the actual content.
It certainly dissuaded me from ever posting any other conversions or fan projects here and instead finding other ways of distributing them to my fellow fans.