The city and road placements are perfectly plausible. The city symbols are a bit indistinct - there's enough other busyness going on that the little constellation of dashes almost disappears.

I'm unclear what you mean with all the dashes in so many areas - they're lowering your contrast, making the rest of your symbols convey less information.

There *are* styles of old maps that have widely separated symbols like you have, so if that's the style you're shooting for, it's fine. It does have the effect though of making the mountains seem like individual separated peaks rather than a range. Overlapping the symbols carefully would better show a linear feature instead of a hundred point-features. Even if you just crowd a string together that's another distinct antique style.

The center-north to mid-southwest river has issues. Think about how that path manages to be downhill all the way from source to delta. Take that dead-center set of hills. In general, the slope of the land has to be downwards from there to the sea to the northwest. Sure, that's the *average* slope, and a sufficient ridge right at the coast would "keep the river from running into the sea" there. But you don't show such a ridge. Water flows downhill alone (duh) so it would hardly be flowing *sideways* across any real terrain. Look up the "How to get your rivers in the right place" tutorial - it's stickied so it shows up at the top of the Tutorial forum.

The eastern swamp would be a sight more believable without the explicit stream channels. What's your scale? You wouldn't have to show what would be alternate paths to the sea over too vast an area, if you just showed a few rivers entering the swamp. See that eastermost river leaving the swamp? It goes from what your smbology implies is pretty much sea-level swamp, through drier woodlands, which one would presume were drier because they're *higher* than the swamp... don't want to be showing water running uphill, do you? :-).

It's got promise - keep dinking with it and it'll turn out okay.