I'm doing a lot of thinking about different things right now. First things first - you say you have to have everything planned out before you start a map. I'm the opposite way around. Very "Bob Ross". Things just happen in a map because they happen. I've put a cursed/sunken city in the middle of that humungous swamp area. It's just an idea. Maybe it helps - maybe it doesn't. You choose if it stays or goes away. Please let me know what to put there instead though if you want it gone.

The other thing I'm thinking about is scale. How big are you planning to export this map? This is the area I've been working on today between other jobs, extracted from a full export at 3000 px on the longest side. At this scale the structure symbols may be a bit small to do their proper job as symbols. 3000 px at 300 dpi is a print that is 10" in both directions when printed out. I think that's probably already too big for an A4 sheet.

I've been using a lot of artistic licence on the design. If that's not ok, please say.

If you want to know how to make the shaft look like a hole, there is this video by Remy - towards the end of it:

Is this better?

The reason I'm adding the real world names is to give us a reference for further instructions. It's easier if you say change "Fred" to "Burt", than if you give me a lengthy description of where you want a label that doesn't exist yet.

So this is going to be a historic fantasy of sorts - a mixture of actual history/legend and fantasy?

You may have to be a bit patient with me over what goes where, since I have no familiarity with the area at all. I'm also not good with pages and pages of text. Easily lost, you see. Much better with well-timed short bits of info ;)

Found Grand Traverse and Mission Point. There's not really enough room to add the name of the peninsula as well, but that's probably better done by a smaller regional map when Quenten gets going on them.

I missed that bit! I must watch it again and see if you're right :)

And thank you :)