Kris and Scott work in the same office in Seattle with PA and (last I checked) he didn't give up the dream; ChainSawSuit and Starslip are updated multiple times a week.
I like Scott as well, and I probably would hire him for this as he has the perspective and the willingness to get the job done, even if it offends people.
But I'm not from a syndicate and if I get my way, I'll help flush them and book publishers out of existence :D
1) Scott's popularity is partially related to his friendship with Penny Arcade.
2) Scott's "expertise" didn't save his best friend Kris Straub from giving up the dream and getting a job.
3) Howard Taylor has a full family, so him having financial trouble is simply more likely even if they were close in income.
I like Scott, I just wouldn't hire him for this.