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So a while ago I posted some musings about freeform city creation and I've been using them for my campaign for the past 6 months. It wasn't that bad, the hardest part was finding higher resolution images of the buildings. I tried making them myself using vector art programs but that was a bust. So this past week I tried to get DALLE-3 to make building artwork for me, and it did a great job. Just in isometric, grid based fashion rather than in the top down fashion that I asked for. So I used Inkscape to transform my map into an isometric version and created tokens from the artwork. Still a manual process but it only took me a couple hours to put together.

It ended up looking so good I had to share it.
Old map (taken immediately after a certain city event)

New map (Taken after the city was rebuilt)

My process.
1. Create a map of the terrain in DungeonDraft. (I typically also place the roads in this step because it is easier than making roads in Inkscape).
2. Create an isometric grid in Inkscape
3. Export the DungeonDraft map as a png then load into Inkscape.
4. Move the map to a "Background" layer then rotate and resize the map to fit the grid.
5. Generate "Isometric strategy game art of a <Blank>" using the AI generator of your choice.
6. Copy the generated artwork into a free art tool (GIMP, Microsoft Paint 3D, etc.) to remove the background and isolate the building.
7. Copy the resulting building into inkscape, move it to the desired position.
8. Repeat steps 5-7 until the buildings are placed.

I wanted to try using XP instead of milestones to really get into the Hexcrawl experience but I'm afraid I can't get the numbers to add up. The milestone they list to reach level 2 is defending Oleg's Trading Post but at the end of Aldori Manor they will have only gained 620xp, and will only get 40 more from the Moderate 1 encounter.

I don't see where they will get the remaining 340xp they need to reach level 2 before venturing into Greenbelt. Unless the idea is it is supposed to include ~8 random encounters along the road to Oleg's.

I'm still pretty new to Pathfinder 2 but my impression is that I'm basically forced to use milestones because there is no way the listed numbers will allow the party to level up at the expected rate.

My gaming group is very excited to get involved with the city building portion of the campaign. But I'm worried that the strict rectangular grid might not appeal to their desire to get creative with their towns. So I'm considering allowing freeform city design using the drawing tools in Foundry VT and Dungeon Draft.

The process I'm considering is to first create a base map in DungeonDraft. Then add special buildings in a freeform manner as tiles. Finally just draw roads using the drawing tools in VTT. Adjacency bonuses would just be awarded if applicable when buildings are connected by a road shorter than 200ft.

Then in addition to building special buildings every time they level up their city they also have to create zoned districts to reflect the attributes and skills they increased (commercial, residential, dense residential, farmland, etc). For example each level up might require 4 acres of new development. They draw them on the map using the tools in Foundry VTT and then I place normal buildings to fill in the space. No need to be super precise. Just get the right feel for it. If they alter the map too much, such as cutting down a forest, I may have to go back to Dungeondraft to get a new base map. I'm not too worried about it since I think they can do a lot just within Foundry VTT itself. There are no rules on where these districts need to be placed, it's just a way to tie city growth to in-game growth and have a bit of collaborative city design.

Here is a shot of what it might look like.
https://imgur.com/a/5RFdZYQ

To get my artwork I'm using StableDiffusion to generate new buildings to populate the town and it is working pretty well. Just draw rough shapes and let the AI do the rest. Although I have to manually extract and convert the buildings into tiles using GIMP.
https://imgur.com/a/gSip6nD

Has anyone else attempted something like this? Other than the headache of making custom maps and artwork are there any mechanical implications that I might be missing? I plan on updating this thread in a few months after we've had a chance to put it into practice.