$375 million in today’s dollars would cover (adjusted for inflation) the marketing and development of Call of Duty: Modern Warfare 2. https://en.wikipedia.org/wiki/List_of_most_expensive_video_games_to_develop

Is there a reason this requirement doesn’t apply to iMessage as well?

IMO the best way to ensure that traffic always goes through a VPN is to use network namespaces. The wireguard website has an article describing the process. In a nutshell, you create a dedicated namespace to put the physical interface in, create the wireguard interface in that namespace, then move the wireguard interface to the root (“normal”) namespace. That way the only way to get traffic out without the VPN is to run a program in that dedicated namespace.

know their game is more expensive on switch than on pc, but it’s well within your budget and you want to give them extra coin

With the (probably doesn’t need to be stated but here I go anyway) caveat: how much of that coin is going to the dev, and how much is going to Nintendo? The game might be cheaper on (for instance) Epic, but Epic takes a smaller cut.

Passkeys (which are broader than just Apple) and this are not related at all. Regardless, Apple absolutely has interest in controlling browsers. Hell, they already do it on iOS, where you can’t use any rendering engine other than theirs.

The only reason they might be against this is because they feel they can’t control it the way they want.