http://www.apastyle.org/learn/faqs/when-use-h...

"General Principle 3" :

Most compound adjective rules are applicable only when the compound adjective precedes the term it modifies. If a compound adjective follows the term, do not use a hyphen, because relationships are sufficiently clear without one.

• client-centered counseling

but 

the counseling was client centered

• t-test results

but 

results from t tests

• same-sex children

but 

children of the same sex

Oder funktioniert das mit dem Bindestrich bei Adjektiven komplett anders als bei Substantiven?

Rulebook can be all one word, which of course makes the question much easier: rulebook-compliant

https://dictionary.cambridge.org/dictionary/e...

rulebook

noun [ C usually singular ] UK ​ /ˈruːl.bʊk/ US ​ /ˈruːl.bʊk/

a book containing the official rules for an organization or activity

https://en.oxforddictionaries.com/definition/...

• The regulations or standards of behavior that should be followed in a particular job, organization, or sphere.
• ‘a lot of bands decided they were going to tear up the rock rulebook and start again’

What about a fifty-year-long marriage? Or young-people-oriented?

I don't think I'd say either one. Instead: a 50-year marriage (or fifty-year marriage) and youth-oriented. Other than that I agree with #2 and #6.

"rule book–compliant" (using an en-rule rather than a hyphen) (#6)

I've never seen that.

I've never seen that.

Well, Chicago do say "This editorial nicety may go unnoticed by the majority of readers ..." (;-)

And "... nonetheless, it is intended to signal a more comprehensive link than a hyphen would. It should be used sparingly, and only when a more elegant solution is unavailable."