Ian should win this. He definitely has advantage on this indoor court, and likes the overheads. He is also very familiar with the whole setup/environment, which is almost like a recording studio than a tennis court.
But..... I think the better win for Ian would be if he lose this match.....train for couple of months.... and bring GSG again and win that match.
This will allow more content (including all the future training, things he found as issues in the first GSG match, and fixing it, and then implementing/executing it in the second match) and more drama for Ian, which seems to be the way Ian is directing Essential tennis channel towards.
One thing I really like about Ian is, he is willing to think differently, and make use of the internet age differently. He knows that people are not going to "pay" big for all the content anymore in this age, and instead of trying to fight for dimes with other internet coaches, he is leading the way to a new tennis reality enterntainment, and experimenting to see if that makes more $$$. Again he does that all these in a transparent way (without making shady claims, like 120mph serve in 10 days). In the end he has a family to feed. If he can make $$ , have fun, do things he like and make it enjoyable to audience at the same time, it is a win for all.
If Ian wins, everyone will say that was expected. But if he loses, there will be lots of comments about Internet coaches. Lose-lose situation.