I think the whole point of drawing by hand is to create something that does not look perfect, and that gives it more integrity/realism. So yeah, this compass rose definitely has character, as does the border (one of my favourite bits). I didn't think of the Spanish main until Diamond mentioned it, but now, that idea really suits it.

There's something about the swamp. It looks good, but somehow wrong. It might be that swamps usually form along major rivers (I think)? or the fact that it ends rather abruptly (maybe stretch it along the coast for a while, so that it becomes really elongated)? or maybe something to do with all of those streams?

Like Diamond says, though, keep it up.

As for motivation, I've found that I make my best maps (and enjoy it the most) when there's some kind of story to tell. Otherwise you're just making pretty scribbles which have no practical function. That's why I invented Larithas Stone, to tell a story through maps. I don't know how you use these/why you draw them, but maybe this approach will give you that boost you're asking about.