Building a settlement from scratch, how much progress by month?

Lanefan

Victoria Rules
I use Building value/Labour/10+skill = Days

The DMG says a Guildhouse and Trading Post can be built for 5000gp, I’ll assume the same price for a Hall (Longhouse/Barracks). so if I have 5 unskilled workers

Hall 5000gp/5 workers/10 (skill) = 100 days
Of course if you have more workers or a Proficient Carpenter then the job will be done quicker.
Nice simple formula. I like it. :)
You can extrapolate to build a village allocating your fixed pool of Labour Remembering though that Food harvesting also needs Workers to attend to it - indeed for a new colony the first 3-6 months should be focussed on food supply and avoiding starvation
Assuming no external supply lines, this is true. But if there's supplies available from "home"* then it might not be quite so important. Much also depends on the climate where the new settlement is located.

* - in the OP's scenario there's at least one resupply opportunity as there seem to be two boatloads of settlers coming at different times.
 

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I don't think it's entirely silly of me to recommend the computer game Banished as a reasonable depiction of the exercise. At basic difficulty you have about 16 citizens, maybe 10 adults and 6 children, along with a limited cache of supplies - food, clothing, tools, and basic building materials of logs, planks, iron and stone. You initially get, what, 9 months starting in early spring to essentially get your town into a survivable state. You need housing for everyone, you need to get crops into the ground ASAP because you're already looking at the coming winter, and then even though you have planks you need to start cutting logs into more planks for building, starting lumber operations to get more logs because a lot of that wood is earmarked for heating and cooking not just construction, and then you want to be hunting, fishing, gathering food, starting to raise animals if you can for food as well as leather, planning on mining sources of iron and stone for still more construction, tools...

If you were to multiply the starting population to equate to 50 adults you might reasonably get some economies of scale, but the tasks needed to get a new colony up and on its feet FROM SCRATCH, aren't going to change a lot. WINTER IS COMING. Regardless of when you start, if you aren't prepared to survive the winter with its requirements of keeping people fed, warm, and safe while also being limited in the ability to do any of that DURING the winter then people are gonna die of exposure, starvation, overwork, illness/disease, or plenty of other varying factors.

If you don't have it ON HAND when you arrive at your new colony site, then you MUST make it, grow it, trade for it, steal it, etc. and even then you need to be working towards being as self-sufficient as rapidly as possible.

If you're assuming a more temperate environment you'll have a much easier time of it - but it still won't be a cakewalk and none of those things that NEED to be done will really change. You'll just be less catastrophically affected if you fail at any of them. And swing that thermometer too far into tropic or desert climates and you have different challenges but no less seasonally timed.

But then that also still doesn't account for severe weather, monsters, bandits...

Yep, all else being equal, I'd say that you have 9 months at max to complete the first major push for establishing a new town/colony - steady supplies of food, water, established security, and crops already in the ground and if not producing already then able to yield something the following spring. If you start at the wrong time of year you're not so much building a new place as trying to survive until the weather breaks and you can begin that effort. So, yeah, within a few months of breaking ground you should have something that looks like a village, even if it's not wholly and safely on its feet yet.

"The Lost Outpost", first adventure in Ruins of Azlant, presents a colony at the 5th month mark (shown on the map image I've attached). They've managed to build:
  • Whatever work needed to clear the settlement site
  • 1 wood-frame mud-brick smithy (smithy+small home)
  • 1 large chapel (logs)
  • 1 large long home
  • 1 log cabin
  • 1 two-story (wood frame, mud brick) government building
  • 2 long wood-plank buildings (barracks)
  • 17 small cottages
  • 2 wells
  • 2 mud-brick sheds
  • 5 vegetable patches
  • Partial palisade (1 finished wall, 2 started walls)
  • 1 small dock
  • 1 canoe
Does that seem unreasonable amount of progress for 5 months' work?
With a work force of 50 people of adequate skills? Mostly, yes. If the construction on all of it emphasizes speed of completion over appearance and longevity. The cottages in particular would probably be fairly slapdash, but they'd be replaced by better, more permanent buildings over time. I have doubts about putting effort into LARGE buildings though, which require better engineering and more work. The emphasis SHOULD be on small constructions able to be completed quickly. The large chapel, "long house", and two-story government building are all dubious to me. After 5 months maybe they'd be STARTING on those with the expectation that they'd be built better and to last. And I'd say a hell of a lot more than 5 vegetable "patches". Without other major sources of food in the area such as by hunting or plucking fruit off the trees and vines, most of the population should be intending to be farmers in the first place. 5 vegetable patches for 50 VERY labor-intensive workers is inadequate to my thinking. After the first year you want to be bringing in enough crops to support everyone for the entire second year if it's at all possible. A vegetable patch is what you have when you already have a market or some other major source of food.
 
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Lackofname

Explorer
If you were to multiply the starting population to equate to 50 adults you might reasonably get some economies of scale, but the tasks needed to get a new colony up and on its feet FROM SCRATCH, aren't going to change a lot. WINTER IS COMING. Regardless of when you start, if you aren't prepared to survive the winter with its requirements of keeping people fed, warm, and safe while also being limited in the ability to do any of that DURING the winter then people are gonna die of exposure, starvation, overwork, illness/disease, or plenty of other varying factors.

If you don't have it ON HAND when you arrive at your new colony site, then you MUST make it, grow it, trade for it, steal it, etc. and even then you need to be working towards being as self-sufficient as rapidly as possible.
Worth noting the presence of supply ships; the sponsors want this to succeed, and thus will continue to invest. Once it's clear the place isn't going to immediately die, they'd be looking at one supply ship a month for a while.
If you're assuming a more temperate environment you'll have a much easier time of it - but it still won't be a cakewalk and none of those things that NEED to be done will really change. You'll just be less catastrophically affected if you fail at any of them. And swing that thermometer too far into tropic or desert climates and you have different challenges but no less seasonally timed.
It's tropical jungle. Analogous to Central America/upper South America and Central Africa.

Those regions have the same climate: A dry season and a rainy season. Going to say temperatures range between the 60s and 80s, with high humidity.
 
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