Usually when I can't find a simple way to do something, only a messy/complicated one, I find it worth popping into the info file and looking around - as long as you're comfortable using bash-specific (vs POSIX) idioms, there's often some generalization that helps. (Having said that, stack overflow "isn't great until it is", I've found some real gems of "can't you just do this?" that vastly simplify what I was trying to do by, effectively, doing something else entirely.)
That said, I think with bash (and anything with a man page more than 5 pages long - "screen" and "lsof" for example) it's worth just doing a quick skim of the entire man page once every 5 or 10 years - sure, most of it will be "yeah, I know that", and a bunch will be "... who asked for that? why do we even have that lever?" but there will be a few things that fix something that's annoyed you for years, and a few things that you'll ignore and then 6 months later you'll say "wait, I read something about this" and go back and fix the problem.
(Reading the changelogs of your primary tools is also smart, and I'll admit I pretty much only do that when looking at security changes, or when looking at a weird behaviour change between releases and trying to figure out what the intent was - not that I recommend that part per se, you just become the greybeard everyone comes to with weird questions :-) Most recently, bash pipeline tail-exec...)
That said, I think with bash (and anything with a man page more than 5 pages long - "screen" and "lsof" for example) it's worth just doing a quick skim of the entire man page once every 5 or 10 years - sure, most of it will be "yeah, I know that", and a bunch will be "... who asked for that? why do we even have that lever?" but there will be a few things that fix something that's annoyed you for years, and a few things that you'll ignore and then 6 months later you'll say "wait, I read something about this" and go back and fix the problem.
(Reading the changelogs of your primary tools is also smart, and I'll admit I pretty much only do that when looking at security changes, or when looking at a weird behaviour change between releases and trying to figure out what the intent was - not that I recommend that part per se, you just become the greybeard everyone comes to with weird questions :-) Most recently, bash pipeline tail-exec...)