I'm not intimidated, and the things you mentioned aren't that complicated. what I don't get is all those stuff about what makes a font good. I can spot out flaws in ux, recognize a good ui solution from a bad one, and I see when something falls off the grid, ohter than those technical sides I like photography, illustration and many other forms of visual art, etc., I enjoy looking at good type, but with all of that I have literally no idea why designers say arial sucks (I know comic sans suck though, fortunately). what I always do with fonts is basically a negative selection so the end result is legible and doesn't look awful for my taste, but I'd f.ex. find problems mixing serif with sans correctly (serif is in general a mystery to me, I use sans as a safer bet).
Typography is hard, if only because it's quite subtle until you really start paying attention to it (in everything). How good or bad a typeface may be is irrelevant beyond a minimum quality, e.g. it's kerned well, it has been pixel hinted. It's simply a question of appropriateness.
The reason Arial is often, arguably inappropriately, slated as a bad font is because it stacks up poorly against other fonts in the situations where it's appropriate. Helvetica is more sterile, balanced, and tasteful — it does most of the things Arial does, but better. The only advantage Arial has over Helvetica is at smaller sizes on the web, where the head of the t, tail of the g, and terminal of a help to make the characters more distinguishable (in theory).
So beyond quality, it's about what's more appropriate. Then of course you've got to set it well, but that's practice.
this presentation I watched some time ago is cool http://www.organizedwonder.com/videos/310 although as with arial, I couldn't tell you why helvetica is bad.