This one didn't quite go so well and I'll likely make another attempt at some point.
The core plan was to go for quests with a decent RP reward and aim for either a gold or platinum in them while using the spare time to fish for random events through patrolling the seas.
However various things went wrong, firstly the Foolishness quest bugged out and the jester never sat on the throne which resulted in me needing to exit out of the quest. Additionally going for the options which provide RP rewards tends to just get them injured or get them other penalties. As such it'd probably be better to wait for the second or third quest, when the hero sim has actually got a decent chance of getting RP from the boat events before trying it.
I'm also fairly sure the training ground added by building the barracks counted towards my total number of buildings which is why I did a double-take near the end as that very much threw off my calculations I did beforehand.