This is a really slick faction. Everything seems to flow together and each decision informs the next. Prosperity leads to more Workers, which means more work gets done by the Guilds, which encourages expansion and more Prosperity, etc. Sounds like a growing City to me!
Are shanties considered Guilds for the purpose of scoring? I think they are (since they're in the same list as the other Guild tokens), but just wanted to mark sure. Seems like it would make an interesting decision for the other players: attack a large group of combatants (and potentially suffer loses) or let them score a free point!