Hi,
You may want to consider posting the question for the WSA in the Web Security section if you have not already.
As for the ESA questions,
You can filter files , using either content filters or messages filters. The ESA has the ability to do this based on file type or file name. File type is generally a better option. You can also filter based on files size.
For email filtering I am guessing your referring to filtering or blocking based on a a specific sender or recipient address. This is also possible using filters and policies on the ESA.
You can filter content such as Profanity using dictionaries. You can utlize the built in dictionaries or you can create custom dictionaries.
For data loss prevention, the ESA has an optional feature , DLP (Data Loss Prevention) that does offer this functionality.
The remainder of the options you mentioned would be covered under WSA functionality and would be better answered by a WSA engineer in the WSA forums section.
Christopher C Smith
CSE
Cisco IronPort Customer Support