Don't get me wrong, I hear what you're saying, and I'm not entirely unfamiliar with the concept of putting effort into making quality engineering look nice as well. I think it's an area which is only really developed in "luxury" items, though, where customer perceptions and the "feel good" factor are as important as the functionality of the product.
For example, I fully expect the parts of a mechanical Swiss watch to be highly polished and machined to within microns, even though I never see them. Knowing that they're there, and that they've received all that attention, is part of the product offering. And, of course, a watch made like that sells for 10 or 100 times the price of a quartz watch, which probably doesn't look so different on the outside, and actually keeps better time.
I think it's probably fair to say that every product I've ever designed has been functional - first, last, and everything in between. People buy products I've worked on because of the features they have and the quantifiable aspects of quality: reliability, cost, size, power consumption and so on. My PCBs all live inside boxes, are never seen or even considered by the end customer unless they go wrong, and they are judged only by how well they work. And that's absolutely OK with me.
If I were designing really high-end hi-fi, for example, then things might be different. I'd expect reviewers to be opening up the box and showing photos of the PCB to potential buyers, and I'd expect those buyers to judge the product based as much on how nice the board looks as on how the system sounds. I would indeed put a lot of time and effort into making parts line up, or to have circuits be exact mirror images of each other, or whatever - not because doing so improves the sound, but because non-engineers will look at it and perceive it to be a quality product.
Example: try an image search for "Oppo BDP-95", and look at the audio board. It's a high end Blu-ray player, and the manufacturer has clearly put a lot of effort into making this board look like what you might expect to find inside an expensive model. But there's no way that board is actually optimal from either a cost or performance point of view - it's twice the size it needs to be for starters, and long traces generally pick up and radiate more noise than short ones.
I would suggest, though, that 99.9% of PCBs are never meant to be looked at, and nobody is ever willingly going to pay me for the time it would take to make a board which is a functional work of art. There is no reason to.
On the subject of fonts, I completely agree that they're important when they're used in a medium where they'll actually be read and appreciated - but few people outside the industry ever even see a bare PCB, and when they do read the silk screen on the board it's for a purely functional reason.
The lettering on a PCB needs to be clear (which is generally a limitation of the printing process, which varies a lot between PCB fabricators), and it needs to be positioned logically and correctly. The intended audience is a handful of people involved in the manufacturing chain, and they care about correctly identifying part numbers, component locations and so on.
The end customer, whose opinion on aesthetics might actually matter, is unlikely to ever even see the board.
For what it's worth, the CAD software I use offers no choice of fonts beyond size and line width. As you mention, characters are stored and reproduced as a series of straight lines, and that's it. I can import graphics from outside (such as a company logo), but even that is a time consuming process with multiple steps, and not something I would ever do just to change the look of my board even if I wanted to.
Believe it or not I'm genuinely interested to hear what you find out, but I'm afraid I think you may be looking for ideas and inspiration in a pretty dry, empty place. Sorry.