I like the tailoring guild idea. I own a settlement with tailors being the second most abundant profession in the settlement. It's in the grasslands so textiles should be plentiful and Neran is the largest tribe with Dras second. If you wanted to start a tailoring guild I would be open to joining, I plan on having an alt focused on tailoring. I can set up a tailoring guild hall for free in my settlement so we would have space to work/meet and I can lend you housing for free. PM me if you are interested

Considering what you are looking for, I think you should perhaps contact the Duchess of Drakeolm in Blackheart. Tenslea there is of the Dras Darkholm Royal Family there so definitely Dras connections but she will be ruling in the Neran portion of Blackheart where you will get mostly Neran flavor and choosing options for you personally.

Also I know she used to be very interested in Tailoring and clothing making so it might be a great fit for you.

My city is not centered around tailoring but I think your courtesan guild could be a good fit. The main religion in my city follows the Two-fold queen. She believes in balance a light and a dark side.. There is a river that runs through my city. One side of the river, there would be a just/simple way of living (bounty hall, adventurer's guild, food, and the necessities) and the other side not fully illegal but things like gambling, finer foods, maybe a geisha house. The To' resk, waerd, neran, and janoa are in my town.

My kingdom has a tailoring guild and they are all about clothing design. If you are interested in joining them I can give you their discord.

Send you a message.