[quote=@MacabreFox]
What would be the process to becoming a city guard? How old does one have to be? Or does Windhelm have its own army, before 4E 201? Is there a type of conscription? Trying to find something militaristic for this guy to do before the war, as he would be 27 when it started.
[/quote]

Ask one of the guards, get in because of able body and having lived in the city for long?