IPAD?! Are you kidding me?! I can't wait to see how this winds up. They keep saying iPad is the way of the future for art, but I wouldn't want to try drawing a map on mine. (Although, I guess you're using a stylus rather than your finger? That probably makes it like drawing with a graphics tablet, huh?)
Well, I don't know anything about Procreate so I don't know what limitations the programme has. And I'm not entirely sure what you mean with your list of requested advice, but so far so good. The mountains look great to me. There's a few spots of river that either break off from what looks like lakes or that are broken in several places, which doesn't quite make sense, so I'd suggest taking a look at the thread about how rivers work (it's around here somewhere, not sure where). Also, the tree-tops inside of the coniferous/pine forests kind of look like tiny mountain ranges, so you might want to round them off or shrink them down a bit. The other trees look great, though, and I like how you've woven them around the hills.
People tend to settle where there's fresh water and natural transportation routes, so frequently in the forks/bends of rivers. Unless your world is populated by winged species or people who can magically/technologically manipulate rock and stone, they also tend not to settle on the top/sides of mountains, so it's usually best to put your cities and towns on flat land. That said, miners often settle at the foot of mountains/hills or a little way up. And if they know how to build boats for fishing and sailing, there'll be a lot of port towns on the coastline, especially near rivers, bays, and estuaries. Most people don't settle on marsh or swamp land, or regions that flood, but there are historical exceptions such as Egyptians along the Nile where farmers relied on annual flooding to rejuvenate the soil, and there are places in Southern USA with stilt houses in the bayou so you could possibly populate your marshes/swamps if you can explain how they survive there.
Basically, settlements need three things: fresh water, food, and building materials. Security is at the top of the list of priorities for any settlement, too, but can be artificially built as long as the first three things are present.