Hi Tyler,
When choosing a scale, if the block is rightly resized but its annotation aren't, you simply need to make the texts and/or dimensions annotative. If you make the whole block annotative, it will be rescaled alongside the annotations which may not be what you want.
If you want to automate the process, use a .lisp routine. I'm not good with it but you could follow the blueprint of that one :
https://forums.autodesk.com/t5/visual-lisp-autolisp-and-general/set-annotative-using-lisp-or-vlisp/t...