So.....took a look at the passenger wheel, and it was completely loose. Tightened it up and all issues went away -- no bearing issues at all. So I guess I've been driving 40 miles with a wheel about to fall off. Man I feel stupid lol. Glad it won't require a replacement though. Lugs are slightly worn though, so if it comes loose again I'll have to replace the lugs.
Now to find a blue, manual Insight without any downshift grind, for a decent price, near home. I just might've gotten my dad interested in one.