You either hate it or love it. I love it. I hated oblivions map. I could never zoom out to get the entire map. Now with Skyrim I feel like I'm on google earth. I have a couple tips to make it a little easier using the map, very simple tips. Most may already know these.
1. Make sure you press down on the right stick to get a good top down view. Then when you press zoom(R2) hold it as you move the cursor around the map. The reason you hold it is because if you don't the minute your looking down on higher elevation like a mountain it automatically pushes the view back up, so now when you get to lower elevation it's harder to see because the camera view is higher up. So holding zoom will keep the view closest as possible.
2. Many people are upset there is not a way to quickly pull up the map. I found one you do the steps every time you look at the map. The problem is you don't do it quick enough. So what you do is tap circle and hold down, almost at the same time but not quite. So it's circle first which brings up the menu and hold down to get to the map. At first it may be a little weird to do it that fast and it may take a second to get familiar with it doing it fast but after you do it is a quicker way to pull up the map. This also works with the other three parts of the menu. Just circle and hold the direction you want.
These things are very simple, it may help if these things are a problem for you. As far as using the maps to actually see roads and navigate, forget it, I don't think Bethesda ever intended for you to be able to find the 'easy' route to anywhere. At first I hated this but within a few hours i loved it, it makes you stray from the beaten path and find all the wonderfull things skyrim has to offer.
Also in Whiterun at Dragonsreach upstairs somewhere there is what seems to be the a war room. It has a few map around. You'll area map on a table that has little flag markers. If you press x on them your map will update showing you where these places are. It doesn't allow fast travel after it updates but it they do show on the map now. Make sure to activate each marker.
Let me know how this works out for you and please post any tips you may have.
One more tip and probably the biggest. Use the paper map that came with the game or better yet the one in the game guide, that one is incredible and almost worth picking up the special editon guide for. It also has a great interactive map you can use on your computer.
