Here is a crude map. I would like to apologize to the original creator of this picture for mutilating and scribbling all over it.
1 - The Drow Caves
2 - The Cliff Nest
3 - The Hill Fort
4 - The Forest Camp
5 - The Pirate Island (The yellow line marks the edge of the shallow water, beyond which they rarely sail.)
6 - The Abandoned Galleon
So, each group could start in the following location:
Healergirl, Ixy and RubySlippers - Maybe on the northern edge of the forest camp territory? Are you going with the finding a washed up Ixy for the start?
Helenia, OfDelusions and TheHangedMan - At the Hill Fort. Are you arriving, already staying there for a short while or just leaving?
Shihong and Tagan - Maybe east of the Hill Fort.
Aether - Pirate Island. Doing what, about to set out to gather supplies for your ultimate project?
KingandFatherland - Already discussed, you'll end up somewhere near the Hill Fort.
Also for Ixy, Shihong and Tagan: I assume you were on the same ship (the pair of you fell off before it ultimately sunk to explain your different location). How well do your characters know each other?
Question how is land use dealt with I wanted to buy a nice cave with some natural springs coming off her land, the water free to all to use if they come in peace but the cave a druid home and it would also be a holy place. Maybe between the forest and human settlements.
The deal for getting the cave would have been to allow free access to the water except if any pool is inside the cave or used for druid rituals maybe a small one with standing stones to a side.
I wanted to drop a good portion of her money on that as one valued resource under her and the druid communities care.
Deduct either 500gp for an area in the north of the forest (represents an agreement with a tribal elder) or 2,000gp for an area in the south of the forest (represents an agreement with the Hill Fort which is more solid and the tribes won't be too bothered).