Some people are nervous about all sorts of things, and it could be just a coincidence that he's drawing it out with you, a newbie who doesn't know better. I suspect not though.
Stop leaving messages and having whatever email discussions you're having. Tell him that if talking to you live would ease his mind he should call you (like a normal client) to make a booking. You're not going to get into a nice chat on the phone, tell him what you had for breakfast or do whatever it is he wants may require to convince him that you're not a robot. If that's not enough to set his mind at ease then you'll have to say sorry, there's nothing more you can do.
If this doesn't go anywhere don't feel like you should have been more accommodating. If he's just after free jollies, which he probably is, doing what he wants isn't going to get you anywhere closer to paying your rent.