"An old drunk man" sounds like a drunk man that has become old, or is selecting the old person from a group of drunk people.
"A drunk old man" sounds like an old man that has become drunk, or is selecting the drunk person from a group of old people.
The "drunk old man" is the situation most frequently encountered.
Consider using only one of the adjectives...
You're an old man:
You're a drunk man (N.B. not "You're a drunk, man")
The first is idiomatic; often heard. The second sounds strange. It makes sense, of course, but when and how might you hear it being said? Rarely, it seems to me.
I think your OSASCOMP rules apply - in my opinion you're drunk, old ...
It totally works for me. I'm totally into it. Or I'm way into it. These are fine for conversation. But for formal writing, I'd use "quite". "I'm quite used to it. "It quite works for me." "Indeed" is nice to use formally. "It works indeed for me." Or "It indeed works for me." Or, more naturally, "It works well for me." (You know better than to say, "...
For your first question:
To my knowledge, there is no rule about the sequence of "ofs". It depends on the name of the organization.
=> I am a member of the Latter Day Saints of the Church of Christ (or whatever).
=> The Department of Defense of the United States of America.
=> The Ministry of Finance of France.
For your second question:
the Head of ...
Agree can be either used as an intransitive or transitive verb, so adverb comes after the verb.
I fought bravely
I ran quickly
For transitive verb, it comes after the indirect object.
I do not agree with him totally.
Y'all shouldn't be askin' these questions. Chucks, almighty! You folks figgerin'on gettin' here with us Texans?
"I hope you ARE ALL doing well."
"You all" is American dialect (especially Texan, as far as I know).