Are you required to hire a trademark attorney to submit a TM registration application?

No. You are not required to hire an attorney. The US Trademark Office says “A private trademark attorney (not associated with the USPTO) may help you avoid many potential pitfalls.”

How do I respond to a ‘likelihood of confusion’ with a registered trademark I already own?

You can claim ownership of a prior registration by amending your trademark application. This may overcome the Examiner’s refusal.

Can I trademark a version of the US Flag?

It depends. There are many registered trademarks that incorporate common aspects of flag. If you would like to see some of these registered marks, you can search.