Things like this should be led by who is best to ask.
Imagine you're in an open plan office. To your left there's a design team (us). To your right there's a tech support team (superuser/adobe.com). Which team do you ask?
You'd ask the designers if you want answers based on experience with design tool advanced features and finding workarounds to create something to certain specifications. A tech support person would say "the software is working correctly but this is not in the list of supported features", which wouldn't help.
You'd ask tech support if it's about routine computer use or maintenance: installation, crashes, memory issues, hardware compatibility, "Help my motherboard is on fire", etc etc, because that's in their professional expertise and not in the designers' professional expertise.
So for the examples listed:
- Exporting OTF: It's about using a design plugin to create a design file to certain specifications: advanced use of font file formats. I'd ask the designers because getting the most out of font file formats is something that some designers do, whereas I'd only expect tech support people to deal with fonts from an installation and licensing point of view.
- Photoshop copy CSS: It's about working around an issue with a design program to create output to certain specifications. I'd ask the designers because we come up with workarounds for issues like this every day, whereas tech support would simply say "Photoshop is installed correctly but does not support this feature the way you want".
Examples of off topic questions would be things like "I installed Creative Cloud and it keeps endlessly asking me to log in" (Adobe forums) or "I installed a font and it isn't showing up in my list of fonts" (superuser for Windows, Apple.SE for Mac).
As for some people liking these questions and some not: that's what tags are for. If we think this is a real issue, give them a consistent tag like
technical workarounds or something, and technical-minded designers who like them can add them to "Favorite Tags" and people who dislike them can add them to "Ignored Tags".