I can confirm the problem Quenten reported. At a guess, it may be to do with the CA187_MediumIslandChain.esc file (I'm not familiar with the file type, so don't know what to open it with to check). That's the file being accessed by the macro that runs the drawing tool, at least, and it seems to be the main difference between the three Island Chain drawing tools from a quick look.

You can just use one of the basic landmass drawing tools in the style to do this. Note you can also delete individual islands and replace them this way (as I just did a quick test doing precisely that).

Debris on the lower floors looks a little flat; as if it's part of the floor itself, not sitting on it.

Also, if the structure is stone, the fractured edges look odd. Generally, if damaged, you'd expect entire stones to drop out, or parts of individual stones, as well as leaving surface damage to those that survive. The very fiddly raggy edges that cut slightly into neighbouring stones and wander across others look very unnatural. Right now it looks very like the floors are made of thin sheets of acetone-melted expanded polystyrene.

That impression is also reinforced by the lack of stone debris on the floors below; it just seems to have vanished.

You might want to tweak the shadows on the upstanding parts of the battlements; it's strange to have the same length of shadows from them on the ground as on the roof, as if the roof's floor is actually level with the grassy surface, and the tower's interior is really below ground.

Certainly, I found drawing "Naughty Lass" quite a challenge overall. There's a particular complexity in trying to visualise things in 3D to be able to draw 2D versions from top-down and side-on viewpoints, and deciding exactly which line you'll pick for the cross-section, etc. There isn't an ideal solution, so you end up just picking whatever seems to work better, and hope users/viewers will be able to tell what was intended.

There is a similarity to the cross-sectional views of caves we've discussed before here, though with a ship, you can't usefully vary the line of any sections, as that just makes it still harder to draw for a vehicle.

I'm not saying it will definitely help, as I'm not sure what changes were made when the Ships Annual was updated, as they were drawn only using the original, but I had to handle similar deck-level elements, and other features, when designing "The Naughty Lass" for the Atlas. For ease, you can pick up the deck plans FCW here, and the sideview here, in case those may assist.

Note though that I did "cheat" with the yards, by having them piercing their respective masts, partly because it's a magical vessel, partly because I was trying to avoid needing to show the complexities of the rigging...

Looking at the base drawings you're working from, and dependent on how close a copy you're trying to make of them, it's worth studying things in some detail before going further, and thinking-through exactly what's being shown.

For instance, it looks to me as if the full width of the vessel at the waterline hasn't been included in the top-down plan drawing. There should be a sliver of the broadest part of the vessel's sides visible below the cannon barrels, which obviously isn't shown on the plan view.

As a perhaps more significant element, the masts are not all vertical, but at a slight angle (hence why they're not illustrated as circles on the original plan view), they're not all of the same dimensions, and you seem to have missed the bowsprit entirely (or rather, you have a broad linear piece of wood texture at the angle and placement as shown in the drawing, but drawn as if it were merely a flat piece of the deck). The latter will be especially problematic, as the original drawing doesn't seem to indicate its full length (it should extend well beyond the bows, for instance). There's the further complication that it should have at least one yard suspended below it, partway along, to carry the spritsail. You may have to busk this from the 3D model images in Remy's posting, I suspect - much as with the features of the upper parts of the masts, i.e. any crow's nests (which should probably be shown as the ship's highest "level" in an FRPG drawing). If you're intending a vertical cross-section for the ship too, you'll need to think-through where the yards are on the main masts.

There are other features that would benefit from further consideration (beyond what Sue and Remy already noted) - e.g. the hatch covers - but this is already running longer than I'd intended, and I haven't time for more currently!