...and get someone that uses Photoshop well to 
     digitize it properly.

Eh, from what I can gather Horrible Logos Guy seems to possess actual graphic design talent, and would likely be more than capable of properly digitizing any given logo. He actually offers high-res copies in exchange for larger quantities of beer, if you dig deeper into the site.

I'd surmise that Horrible Logos Guy could probably create good logos, but chooses not to, because shitty logos are much more fulfilling to create.

Case in point:

The logo he did for "Get Off My Lawn Records" is recognizable as the face of an old hobo from a picture on a greeting card I've seen 1,000 times at stores like Spencer Gifts. In the picture, the hobo is giving the middle finger, and the card usually says something like "happy birthday, go fuck yourself."

Sketch: http://www.horriblelogos.com/wp-content/uploads/horrible-log...

Orginal: http://3.bp.blogspot.com/-jmlJwQlujeY/TilxbkpypMI/AAAAAAAAAi...

The fact that he sketched that up in like ten minutes, and that it's recognizable to me, tells me that he has enough artistic talent to source decent photo reference, and trace a crude drawing over it, while staying within the bounds of fair use, and (as advertised) not seriously developing a commercially usable logo. Thus, artistic talent.