I'd be more willing to bet money if I had some indication, preferrably in the form of an Elo rating, that I can expect to come out ahead.

After we cover some introductory material on our site, I plan to recommend people test out play money games after signing up to learn how the software works and get a feel for the game, then take these two tests. I'll try and get some scores from winning, marginal, and losing players so I can make a recommendation for a cut-off on whether to play or keep studying first.