Lately I've been favoring Consolas. It looks different from what others around here are using and it mostly fits in with my rather specific requirements for a drawing font.
That said, I've had to change fonts many times over the years. These are the things I've learned along the way:
*Readability is about more than how well the font translates to PDF or how well it copies. Be sure to consider 'similar characters' ... that is, the number 1 versus the capital letter I. Also: 2 vs Z, 5 vs S, 8 vs B, 0 vs O, etc. It's mostly the numbers that matter there. (I like to see the crossbars on the capital letter I. Most fonts differentiate between their I and their 1, but often one or the other is just a vertical line. If you see that character by itself then you won't know if it's a letter or number until you find an example of the other character. This really matters for me when it comes to part numbers in the BOM.)
*Don't forget to think about special characters, if you use them. I frequently use some of the greek symbols, such as Phi (to indicate phase) and Omega (for ohms).
*TTF is best for PDF in my opinion.
*Not all fonts have a legible difference between regular and bolded text. If that matters, be sure to check the appearance of bolded text.
*Also, some fonts put their underscores at pretty ridiculous distances from the characters. If that matters, check that too.
*When you switch to a new font, and especially if you move from an shx font to a ttf font, you can count on every single piece of text that is in use needing to be resized and/or repositioned. It could affect some or all your templates, title blocks, symbols, etc. The longer the old font was in use, the more things will have to be found and edited to accommodate the difference in sizes between old and new.
*Make lots of test plots. Be sure to do a half-size plot, if it's done like that where you are. Lots of characters look OK at normal size but plot blurry when reduced.
For me the challenge has always been to find a font that fits these parameters:
*no confusion between similar characters
*has special characters that I need
*has to be a standard, non-downloaded, non-purchased font that comes stock with Windows
The thing about stock Windows fonts is mostly because I often do work that requires me to share drawings with others. If I have a snazzy expensive font that I bought that is in the drawings, they won't see it when they open them up. They'll see all the text but in a different font, which may be a different size than the one I'm using.
My most common pitfall here was finding a font that easily distinguishes between 1 and I that also included special characters.
My second most common pitfall was older engineers who felt that ttf fonts were 'wrong' for drawings. They got so used to looking at the same font for 80 years (Romans, as it turns out haha) that they just couldn't get past seeing how different the words looked.
My third most common pitfall was in my standard notes, which are MTEXT that I copy from project to project. There are underscores and bolded text in there and when I switch to a new font, line and character spacing around those usually change.

Jim Seefeldt
Electrical Engineering Technician