Bramble Bailey
Turning the Bramble Warren into an enclosure, protected by a bramble hedge, frees up a lot of space, quite a bit more than I had anticipated. It can help us grow Thistletop into a working stronghold.
The first thing we need, is somewhere for horses. At the moment, they are (presumably) left completely outside, as there is nowhere for them on Thistletop proper - and (even if there was) they would have to cross a rickety rope bridge to get there. We also need to generate more income, if only to support the extra staff we need as the holding grows. However, whatever businesses we build, I would expect them to generate an income that can be ploughed back into development, or siphoned off as income, at some point. If nothing else, they will serve as a pension for whoever invests in them. At this stage I have two suggestions for businesses – a Wood Shop and an Inn.
The Wood Shop takes lumber, our most abundant natural resource, and turns it into something that can be sold. According to the description “A Wood Shop is a facility specially focused on the output of fine woodwork, from simple furniture to custom, masterwork engines of war.” There is (as far as I can see) no specialist carpenter or woodworking shops listed in Sandpoint, so we should have a good market for anything we produce - which presumable includes wooden shields, arrow shafts and pole-arm/spear hafts.
An inn might not sound like the ideal starter business, but we will need somewhere for workers and visitors to stay. Personal guests might be invited to stay within Thistletop, although all the guest rooms are liable to be underground, and some people might prefer to stay at the Inn, just so they get some light and fresh air.
However, that leaves a lot of space that can be filled later. It might be that we choose to put houses or a tenement there, or we could provide core businesses to support residents of any village that develops. There is certainly space for a few trade shops, such as a Bowyer/Fletcher, a Leather Worker and/or a Smoke Shop (creating and trading in smoked fish, meat, garlic etc etc).
I note that we will have about 100x 5ft-squares that can be used for development in the cleared area. That could easily fit two trade shops and a Lodging House Counting the people housed inside Thistletop, (and assuming a twenty-person garrison) that just about takes us to Village size. We would be able to develop enough buildings, outside the boundary to build a fishing 'district', of the same size, without getting to Town status. (according to the size ranges on the PF webpage)
This is one possiblity for further development of the 'bailey' area, with the lodgings, two trade shops and a garden (split into two sections). One of the Trade Shops could be swapped out for a small warehouse & shop, that might be the start of a trade based for Able - however, that will depend (on some extent) to whether our small population can support a 'general store' - although we will certainly have some items to trade into Sandpoint. This would include items from the Wood shop, and from a trade shop (I favour a Bowyer/Fletcher) a few dried herbs from Dru. If we go for two trade shops I think I would add Basketwork in the second, and there are bound to be reeds, withies etc in the forest / river area. :) There is plenty of time to add a fish shed (Trade workshop) for preserved fish and a Tannery for leather treatment, and a dock when we start on the associated settlement.
However, what is built there, and how it is funded, is something for later discussion.
Population calculated on …
Thistletop - 2x barracks = 20 troops. 5 x servants. Robyn, Velma, Dru, Pidget & Goblin. Total = 25. Other rooms are assumed to be for visitors (inc PCs)
Bramble-Bailey - Inn, potentially, 21 (Bedroom, Lodgings & 10 itinerants in the common room). Lodging house - 21 (2x Lodgings, 1x Bedroom) = 42
Potential Total = 67 (Plus PCs as regular visitors). Village Population = 60 → 200.