I don't believe that they've been anywhere nearly as much of "a pain to spend" for you as you're stating. You're just gabbing.
(IIRC some businesses used to give change in $2 to show their "influence" on the area.)
Only time I ever got rare money was a buffalo / Indian head nickel as change in a cafe very recently, not a valuable form though.
I found a bill from the Weimar hyperinflation era. Its face value was several billion (Milliarden). Its only value was as a curiosity.