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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replying to Nehmo Sergheyev, Iggy wrote: If it's a flip, then Acrylic Latex Paint the Asphalt (it will last) or Vinyl Siding with 4-inch Corner Boards. If you're staying, then stay away from Vinyl Siding...it's The Worst siding I've ever finally experienced. That stuff is horrible for anyone staying 5-years or more. It's a dirt and mold magnet and you'll go through painting efforts just to clean it or even to keep it clean.

Aluminum Siding, Painted Wood or Cement Fiber Plank, Cedar Shingles and Stucco don't need any cleaning and don't attract dirt and mold in this and most types of setups. Or, go with Asphalt again. Outside of Masonry or Cement-Board Backed Stucco or Cedar Shingles, Asphalt is the only thing I've seen last up to 100-years with little to no maintenance.

Personally, I think the current style (not blah gray color) works very well for the house and would only suggest going lighter on the asphalt area (pale/light blue, yellow, green or tan) and keeping the white slat gable look...I'd add an Awning Roof or little Portico over just the front door area.

To add a more "Modern" look, you might want to consider one material for the gable walls and another for the rest of the body. But, I see whatever siding you choose with 4-inch Corner Boards probably dressing it up the best and making your job much easier.
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