It would work for a short while. But I heard that they were cracking down on this type of thing. One of their leading submitters was kicked off for taking money to stories he submitted for a company. But after a butt load of e-mails he got re-instated.
But come to think of it, if you make it random enough. How the hell would they be able to track this. And you only really need about 130 diggs on the weekend to get to the front page.
Give it a shot, and let us know how it goes. And I'm pretty sure you wouldn't be the only one doing this. Like Quadzilla said on Shoemoney's show ... the word "digg" = 15,000 uniques a day. So, I'm guessing here he's gaming digg in some way. Good luck.
-Voodooman