The server could just give the requesting device what it needs to display the content in both orientations. That doesn't necessitate also giving it the layout for 10 other possible screen sizes.
While most mobile devices have exactly 2 size, that may not be a good assumption. There are some devices that support split-screen and you would end up with more that just 2 sizes. You could send a list of all possible sizes, but If the split-screen is customizable it maybe not be feasible to enumerate all of them.
Only politicians have to pretend that everyone is 100% equal in every way, because they can't afford to offend anyone. pg, on the other hand, doesn't need to worry about that as much because what matters is whether the startup is successful or not. If there is a pattern indicating that a certain group of people are particularly bad at running a business, why should he take the higher risk associated with investing in them?
Bad idea, perhaps. But why should Apple get to determine what is or isn't a bad idea for one to do with their own phone? (Although I would suspect part of the reason they banned it is to avoid claims of "Apple's so greedy that while they ban so many legitimately useful apps they allowed this one, just because it can break phones resulting in added profits for them from people buying replacement phones".)
Because, Apple is warranty liable for selling an app that basically get you to break your phone either via current replacement plans or the expected lawsuit. This is a money loser and a problem for parents.