Lanefan
Victoria Rules
As you mention plank structures above, that wood also needs to be sawn in bulk, which means one of the first things you need is some sort of sawmill.One needs wood for shacks, and that wood needs to be logged.
Without that, you're left with logs - fine for cabins, palisades, and similar but not so useful for anything more refined...or anything large unless the settlers have a competent engineer among them.
Much will also depend on the composition of your PC group. If three of them are Dwarves, for example, mining and stone/metal craft will become way more important than if they're all Elves. If they're all Hobbits, they'll build farms before anything else. And so on.The point of this game is for everything to be primitive. If players won't enjoy that, this is not the campaign for them.
The difference between boat 1 and boat 2 is "will you be living in a tent or a temporary structure".
Hell, look at The Stolen Lands adventure path, which is sending Pcs on a Hexcrawling adventure in the middle of the wilderness, and then just handing them gold and sayin g "Go build a kingdom" once they've explored it. The only "tavern" is a trading post at the far edge of a territory the size of Maine.
This is more or less that, except the kingdom/settlement/bla is being built at the same time as the exploration.