Would it be best to respond to a Cease and Desist letter with a letter from an attorney?

Yes, so that you don't say anything that will prejudice you and you will be as sure as possible to definitively close the matter.

Am I able to update a trademark myself?

You cannot "update" a registration unless you are deleting goods and services. If you want to add new ones, you must file a new application.

They are correct. Most if not all people who might see your club name would not notice the difference between the S and the dollar sign, and those...

Am I covered under fair-use copyright?

There is no way to give an abstract general answer to your question. To tell whether someone's use falls under "fair use," you have to look at the...

Registration refused on grounds of Likelihood of Confusion (different classes & mark). Do I have a chance of registration?

Your chances of overcoming the objection appear to be slim at best. The marks are very close and jewelry and clothing are considered to be related...