It is capitalized at the beginning of the sentence or when it forms part of the proper noun or when it precedes a person's name or when it is used as a direct address.
Examples:
Officer Howard Smith
I'll be right back, Director.
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When it's a proper name. For "officer" to be capitalized it would need to be used in a title. For example, Officer Radin made the arrest. However, if it is simply used as "an officer was at the scene," then it is left lowercase.
At the beginning of a sentence and when it forms part of the proper noun or when it precedes a person's name. Example: Chief Executive Officer Peter
Yes it should be, if you mean the DC comics/film character. If you mean the serviceman acting as a personal servant to a senior officer, then no.
The "Executive" is only capitalized when referring directly to the highest official in a government or institution. The phrase "executive session" is not. Conversely, the "Executive Officer" (XO) in a military hierarchy is usually second-in-command to the "Commanding Officer" (CO).
No, seasons are not capitalized.