1st, I think we need to determine what purpose the "breaker on the generator" serves. Art 445 does require the generator to be protected against overload and, if a circuit breaker is used for that purpose, it would be sized based on the generator output.
(The majority I see have been sized by the manufacturer).
Any breaker beyond that point would be sized by as you say "same rules apply".... to protect the conductor and to protect the connected utilization equipment.
Keep in mind Art 445 for the most part addresses the generator itself, so determining loads and breakers is back to Art 240 and 220.
To me, the tricky part can be sizing the generator itself, both from determining loads to taking such factors as "inrush" currents into account.