I wonder how much money Ian is actually gonna manage to milk out of this. I for sure would not pay one dollar for this. Also, this stalling game he's playing could backfire if he pushes it too far, and people could decide to 'cancel' him if you know what I mean.
How is it "stalling"? It takes time to produce such videos if you want a quality product [and I think ET's videos are among the best] and there is probably a backlog so just because the match happened on Day 1 does not mean the video will be published that evening.
The doubles match that's currently the most recently uploaded probably happened weeks ago.
The vast majority will not pay one dollar for this. But the potentially increased traffic will generate ad revenue and other benefits.
Now, if he announces that he was just kidding, that the match won't happen until July, that will turn some people off, never to return. But I'm betting the majority would still tune in come July.