Personally, I've been around long enough to never trust those promises or rely on a "roadmap" of future functionality. If what you have now doesn't meet my needs, you're not getting my money. The "Elite 100" just seems like a sleazy trick to lure in customers who otherwise wouldn't give you their money.
$348/year might be a bit much for a "free-lancer" to spend when they aren't sure your product is something that's going to be of real benefit to them -- and if you require an annual payment, it's not $29/month, it's $348/year.
> "... we couple top-notch freelancers from around the world as a team (usually a designer, developer and any special ops) along with a project manager ..."
I don't have much faith in your ability to "couple" me with unknown people. If the others fail to deliver or are "sub-par", that's going to directly affect my income. Why should I trust my future income to you? On that note, how much of a cut of this team's income are you taking, if any?