Why aren't the files I loaded not working or have a 500 error

The problem in usually in the names of the documents. Linking to documents can be tricky because the URL standards don't allow certain special characters. Things like the "%" or "&" sign will error out. Another thing is computers don't like spaces. For example you can't do is put two spaces in a row in the title. Uses dashes instead of spaced when naming your files. We recommend keeping naming easy.
Instead of calling a file:April 20th Council & Trust Form 25%.docx. Use: Just April-20-Council-and-Trust-Form-25.docx

In Short: before you update any documents, rename them to something simple with no double spaces, % signs, or anything else but dashes or ().

One more thing is to make sure you are linking to the correct path. All files should say: /uploads/files/name-of-file.pdf