I've always disliked the notion that one can 'think into it too much.'
However, in this case, that's a lot of specific effort he'd have to go through in order to do what you're nervous about. The simpler explanation is that it's a bit like how he says.
Is it possible that he's just gaming you? Yes, it is. Nowadays, it's a bit more common knowledge that if you withhold satisfaction from the other person, it will get their attention. Or that if you challenge the other person, it will elicit a strong response (one way or the other), instead of being neutral. So those tactics you mentioned are possibly his attempt to keep your attention.
But even if that's the case, it's only web chat. Until you meet him who cares? If he's gaming you, so be it(...and it's not like women don't game guys too!). You can either enjoy the over-all experience, or not, all good things and bad things combined. Once you meet him, the stakes are quite real. But for now, when you're just typing at a keyboard, where a relationship can't go very far, the stakes are quite low. It's like a nickel slot machine. Go for it, and try not to worry about it.
On the bright side, if he is gaming you, and you keep talking to him, eventually he'll relax, and stop feeling like he has to put up a front in order to talk to you. You'll see the 'real him' either way.