I'm never sure just what's meant by "OSR", but then again, I gather neither is anyone else, as it means whatever people want it to mean, apparently! Not very helpful, however...

If you're aiming for the look of the earliest White Dwarf maps (I was a subscriber from issue 1, though not for decades now; I still have all the originals), their own maps were straight black-and-white, with clear lines and no shading. There was a Midgard map in Issue 2 (1977) for instance, which was just very basic hand-drawn line-art. There wasn't even any shading for the seas on that Midgard map, and if they hadn't been labelled, you'd never have known it! The map did though have a notably heavier line for the coast than the river lines, which might be something to think about for this map too.

I think the first map that used shading in WD (aside from the overland map for the first part of the Valley of the Four Winds story in Issue 8 (1978), which was a piece of artwork in itself, rather than a true map; it was later used as the basis for the boardgame), was the dungeon map for The Lichway in Issue 9 (also 1978; an adventure for D&D). Water was illustrated in that with a similar shading (albeit using a dot-shaded dry-transfer sheet texture) to what you have here, with heavy black outlines for the banks/edges, as also for the outlines of the dungeon walls.

As a complete aside, for all it seems odd now, the square grid for that Lichway map was placed everywhere EXCEPT in the dungeon and across the water - so in all the solid rock only, as we'd likely now think of it. That seemed to work well at first, because the walls were fitted to the grid, so the room interiors were all very clear and obvious, and many of the room sizes could be gauged quite readily. Snag was the vital, very long, broad, diagonal corridor and its right-angled crossways, which ran across the entire southeastern side of the dungeon. I ran Lichway back in the day, and this diagonal element was a nightmare, because you couldn't work sizes from it at all!

Sorry, rambling here, but digging out my old White Dwarfs brings back a lot of memories!

Where is this barony on your main map? That might give us a better idea of what to suggest regarding the vegetation cover shown on it.

If the whole area of the map is heavily wooded, you may be right to suggest you don't really need trees on it at all, but if there are notable clearings, or areas of more open woods, some means of indicating where those are would be necessary. Plus I think you may have taken away the marshy area southeast of Loch Lomond along with the trees, and the other green background colours.

If you need help adjusting the parameters for your road lines, Remy Monsen's live mapping session Modern Streets with SS3 showed how to do this, starting at about 32 minutes in.

During some discussions on another Forum in the last couple of days regarding options for computerised mapping, the subject of Joe Sweeney's excellent videos for CC3 came up, and I made the point about them being for CC3, not CC3+, which has come up here repeatedly, even relatively recently.

Then another commentator said there was actually a whole series for CC3+, posted about three years ago. And when I checked, lo and behold, yes there IS indeed an entire set for CC3+, overland mapping, and another set for city mapping with CD3 added a year ago.

They're all on this YouTube page, with the first overland video here.

However, the ProFantasy tutorials page still links just to the older CC3 videos. I don't think there are any newer dungeon/battlemap video tutorials, certainly, but the links maybe need updating now for the CC3+ tutorials (and perhaps also the zipped download set needs changing?).

I think the newer videos have come up on the Forum before, because I'm sure I watched the overland series for CC3+, but I tend to use the PF tutorials page when I'm quickly trying to find links to pass to someone else, and I know the last time I checked the link for Joe Sweeney's videos I had saved separately, the CC3+ videos DIDN'T appear on whatever that link went to.

The wall drawing tools in DD3 are usually lines of varying thicknesses, I think, which makes it harder to disguise their pristine nature without some extra work - adding rubble symbols, for instance, and maybe trying some additional Sheet Effects on them (as well as Monsen's Color Key suggestion), to give a more "worn" appearance.

Loopysue's suggestion is a good one too - using symbols to make the walls in the first place is a definite alternative. There's the Dungeon Walls Annual issue from 2018 which uses exactly this technique, for example.

Or you could try drawing the walls using polygons instead of lines. That way, you can give any breaks a more ragged appearance as you're drawing them, and even vary the thickness of the wall itself. That will probably need some symbols adding to improve the effect though. Ruins just aren't designed for neat-edged drawing tools!

There is an Annual issue from 2014, the Black & White Battlemaps one, which has a few ruined building symbols in it as well, though they're intended for larger-area overview maps than the usual dungeon maps - plus, black & white only, of course.

I've probably forgotten others too ?