I think this a pretty manufactured example. Does anyone list their skills as an randomly ordered, unformatted wall of text?

All that precious formatting gets lost and the meaning changed if it's copied into a plaintext email (you're back to a randomly ordered list) or printed (color text becomes light gray).

And how does one maintain that cloud? If you get better at something you have to increase its type size, alter its color, and probably change others since items in the cloud are supposed to be sized relative to everything else.

Rather than use a hard to maintain format that you have to explain (is everyone familiar with cloudmaps?), just use words and say I'm not so good at this yet.

Like henning says, the solution is just some simple organization:

  PROGRAMMING LANGUAGES
  CSS 
  Javascript 
  Some experience with SQL
  
  SOFTWARE
  Adobe Photoshop, InDesign, and Illustrator
  Basecamp
  Final Cut Studio
  
  OPERATING SYSTEMS
  Mac OS X and Linux
  Some experience with Windows
  
  Etc.