The behavior I'm looking for is similar to how one can make a path line dashed. Except, instead of being dashes, I'd love to make it show $ signs. Thanks for your help!
Method one - works with any shape.
Create a no-fill, no-stroke rectangle and place a $ sign in the middle of it. $ sign must be on top of the rectangle. The amount of space between the $ sign and the rectangle edges will determine the spacing between the repeated $ signs.
Drag all that to the Brush panel and choose Pattern Brush when asked. Then click OK twice (you shouldn't need to adjust any brush options).
Note: the $ must be art, not type so if you set it as type use Type > Create Outlines before dragging things to the Brush Panel.
Then simply draw a path and click the pattern brush you just created in the Brush Panel.
Method Two - Text on a Path - better for text objects
Draw a path and use the Type on a Path tool to convert the path to a text baseline and then just type $ signs and spaces (or adjust tracking).
This method allows you to treat the $ signs as text still so you can alter the font, spacing, size, etc., as often as you need.