Flush with confidence after closing a $900 million deal with Google, MySpace is taking on its next challenge — convincing advertisers who have put up brand and product pages on MySpace for free that they should pay for “their space” instead:

Now, advertisers say the company is stepping up its efforts to convince big clients using MySpace’s free Web pages, known as profiles, to become paying customers as well.

“MySpace has started to reach out to companies that are setting up commercial pages on the site, encouraging them to reach some kind of financial agreement and forgo the free ride,” says Jeff Lanctot of aQuantive’s Avenue A|Razorfish online advertising agency. “While this could include paying to have the page up, I think buying an ad package to support the commercial page is also a reasonable solution.”

For example, this Wendy’s Smart Square page has 82,025 “friends” on MySpace (you’ve got to love the “About Me”).

Wendy's Smart Square MySpace Page

I don’t know whether Wendy’s pays already for this page, but if they do, you have to wonder why. And if they don’t, you can’t envy the sales rep who has to call them up and convince them to pay. And what if Wendy’s won’t pay? Will MySpace have to tear down the page? That would be a great advertiser relations program — policing for unpaid commercial pages and tearing them down. You can imagine the trade press headlines.

Google obviously thinks it can effectively monetize MySpace — and I think it would be far more interesting to watch and learn from how MySpace succeeds than to watch it fail (despite the inevitable morbid train wreck fascination). But when I read things like “encouraging [advertisers] to reach some kind of financial agreement and forgo the free ride,” I really can’t help but continue to wonder.