Answer 1

I'm tempted to think so based on an explanation for the 'guard' function used to implement 'with...open':

http://effbot.org/zone/JUMP_LINK__&&__python__&&__JUMP_LINK-with-statement.htm

It seems to be preferred because files still close on exceptions:
http://docs.quantifiedcode.com/python-code-patterns/maintainability/not_using_with_to_open_files.html

Admittedly: I'm not able to verify exceptions right now but I'll keep an eye out.