Personally, I think your biggest problem is going to be that WordPress is a hunk of shit and the people who would make good first employees don't work with WordPress because they don't have to - I, personally, have done about at least 50 WordPress installs but I use it as little as possible because the codebase is a festering mess.
I don't know how to get around that problem, but if you figure it out I'd be interested in hearing how.