Request for vague guidance regarding a plot matter

My character is a Shadowy entrepeneur who has legal and criminal revenue streams. Sometimes Mahogany Hall pays you better than people who want to buy those Permits below market value; en Echo is an Echo. No illusions, though - this makes him a criminal and not an honest man.

   He abandoned the path of Urchins/Trickster (with a prominent risk towards the financial allure of Hell) when he fell in love with the Constable.   She saved his soul and he's never (yet) been to a proper Feast.  He's too Shadowy in nature to endure any path that doesn't involve a lot of time in Spite and the Flit, but his time in Mahogany Hall makes him long to go home to a soft bed.  He has never had a boat ride, but is suspicious that that doesn't matter.

  He'll probably eventually end up banished from Court, but having just acquired a townhouse I think he'd rather verify other sources of MW.  He chose the path of the Watcher to escape Hell's influence, having grown suspicious of authority - so the intrigue of the Foreign Office might attract him, but it would matter that the decision was irreversible.  He might not have said all he wishes to a certain heiress.

Is it common to regret pursuing the Foreign Office?

Also, can anybody give me some spoiler-free/cryptic/vague as necessary advice about Business in Wilmot’s End? I have Doing Business in Wilmot’s End 4 and this reeks of similarly permanent plot branches.

Again, not looking for spoilers - just for an idea of what I might be getting into.

Everything in Wilmot’s End is repeatable (barring one option that progresses a story you’ve already started), so no worries about that. The Foreign Office is a neat little area where everything cycles, so as long as you’re truly finished with the Empress’ Court it’s definitely worth going there now that Port Carnelian is open.