Suggestions? House Exterior Covering

https://photos.google.com/photo/AF1QipON8QqsbtH6GSmjCrCFj3WMKS0H-8G7NU0rONqK or https://www.dropbox.com/s/ne5q6wfa23y4lb7/2733-N8th-20161020_184653.jpg?dl=0
What's a cheap way to make the exterior of this old asphalt-composition siding house look modern and decent?
The way the house is situated, only the sides that are showing need covering. The back goes to a concealed yard, and the side to the right (south) is a walkway between the house and the neighboring house.
I know vinyl siding is a possibility, and I'll entertain that possibility. I don't have any personal experience with it, though. It cracks eventually, I understand.
I'm not familiar with how simple paint looks on this kind of material. It seems it would flake off.
Putting up metal and then stucco is another idea. I think, if the windows will be replaced, that should be done first.
Anyway, I'm open to suggestions. If things go as expected, I'll live in the house while woking on it. I'll be able to hire labor, of course. But, other than that, I'm not contracting anything out.
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