A river-technique that might work: assume you're working on the map at 200% zoom. Start drawing a wiggly river up in some mountain area. A given random twitch of your hand when drawing the path might be a couple of centimeters to one side. Call that a 100-km curve. As you get further downstream, zoom in to 300%. Now the same twitch will be just a 67km curve - a tighter loop. Then zoom in 400%, 500%, and so on, automatically producing somewhat "wigglier" river path as you zoom. There's a limit - most small scale (large area) maps will have to have some generalization ... a true depiction of *every* curve would get down into tweaking single pixels!

At your initial zoom, you probably *couldn't* draw a believable lower-river loop or oxbow. Such detail would require precise hand movements of a millimeter or less, and the small curves you managed to produce would be uneven. Zoomed in, such would be easier to make. Even nearing a river's mouth there'll still be large-extent curves, it's just those sweeping wanders will be overlaid with little loops. A way to get the 100-km wanders even far downriver is maybe to use your present paths as just guidelines. Draw your "real" path as wiggles superimposed on the rough path. Go to Google maps and follow a given river from source to ocean, and you'll get an idea of the progression.

This is a generality - sure, different rivers have different degrees of curvature. And really, if you zoomed WAY in on a creek's headwaters, you might see even more chaotic paths, as tiny watercourses avoided each hill and ridge. But at a continental scale, that doesn't show. But if you put in at least some of the progression from less curvy to downright loopy, your rivers will suddenly snap into "believable".

The names are okay. Only the worldbuilder can say what languages have lent names to this or that feature. You *can* automatically convey a sense of patches of different cultures, just by modeling different areas' names on different earthly cultures. At the same time, you can convey that an area has hosted multiple people groups just by purposefully mingling name types. You ought to not overlay the big names (Enorian Empire, Midlands) over the city and town names.

Say your cartographer or your focal nation speaks English, or something like it. It's perfectly natural for him to use *his* countrymen's names for familiar features, even if the "locals" would have their own quite different names. My map of your home would almost certainly term your neighbors Germany and Austria. Yours might label them Deutschland and Osterreich, yes? There's room for grand confusion in a world of nonstandard names, but complexity can build into your world a richness that would be lacking if your cartographer stubbornly Anglicized (or Enorianated) all the labels :-).

When labeling, it's best to distinguish between types of features, whether by font, size, text color, or whatnot. For example, I can't tell if Midlands is a land type, region, a nation, or a subnational political unit of the Enorian Empire. Ravells posted a really good paper he found on name positioning - there's a link to it in his signature.

I do like your map - it has a lot going for it. It's worth further refining.