I agree with this. It can be quite effective if purpose and goals are set out and it's not too open ended in what you expect them to provide you. Being highly organized can go a long way.

I always try to frame around their point of view, not the point of view as a UXer/web designer/ developer etc. What are their goals/their customers goals, perhaps even outside of the software itself.

To me, legibility is the most important aspect to consider for body text, so I usually lean towards using something with proven legibility such as Georgia, or a sans serif like Helvetica or Lato.

For Graphics, titles or shorter lines of text, I would usually pick a font that works for the style/mood/brand etc. This would be where I would look for uniqueness or personality. I have worked on many different types of projects in many different industries so it is often determined in during the style exploration process and is very much project by project.

Hey, I struggled with this years ago and still do. I seem to always be saying this, but what worked for me was to go out and meet people in my city. Meetups lead to connections which lead to job opportunities with mentorship potential. Or you take what you can get at each job and move on when you've gained all you can, be your own teacher.

There are some online courses that could be helpful, there are teachers and other students that are there, but I haven't personally tried that.

Usually the weights are all part of the same font, at least in OSX font book. What context are you referring to?

I've had some luck in checking out local meetups/design support groups in my city. Meet with people in your field in a casual situation. Meet people, get feedback, talk about the good/bad, maybe get some work out of it.

There is the additional concern of trying to use a consistent way of working with mouse + keyboard interactions as with a touch screen.

I think the real thing to consider is, are there aspects of these design philosophies that we can use to strengthen the web, if so, how can we use them to evolve and improve how we interact with the web.

But in all, you're right- these platforms design component libraries to promote consistency on their specific platforms and by extension, in their web applications. The web does not have this luxury/limitation, and if it did, who would design such a thing? There are already many conflicting UI libraries out there such as the popular Twitter Bootstrap that attempt some consistency but in reality, it would be an impossible thing to police or to have everyone agree on a single way of doing things. We can't even agree on a browser.

Sometimes I listen to audiobooks (audible.com), video game soundtracks, but I mostly prefer silence.

10 hour work week.

Meetups! Coffee shops! I would prefer to work with locals and people I meet in person. So a place like meetup.com is useful.