Hello Brennan. Thanks for your request/idea. There are a couple of things we want to do:
First, in the UI, like with Legends, is to have a fitting strategy for rectangle text. For example, multiple columns, shrink text or enlarge box. The problem enlarging the box is knowing which direction. Perharps we can have options like change only width, change only height or change both by maintaining the aspect ratio.
Second, provide a boolean that returns if a the information fits in its envelope. This can apply to area text, scale bars, legends, etc. Having this before the item above would allow you to iterate through sizes until all text fit.
Jeff