KISS works, don't mess with it. the trick is trying to convey alot, with just a little. Make the dot in the i a different shape, or add some flair to the descender of the R in trucking to underline the word, etc... (You know how truckers like their von dutch stuff, though no flaming eyeballs needed here lol) that's where 'adding more while keeping it simple' comes into play.
Your approach for B&W prelims is good. always easier to add color than it is to take it away.
I sorta get the impression that the software is limiting you a bit which is disappointing. I'd like to say grab a pencil and sketch it out if the computer can't do what you want it to.