I’m in virtually complete agreement with John Gruber on this, and I’m also in agreement with The Small Wave on the point that even if the iPhone OS allowed sideloading, we’d hear roughly the same amount of complaining about the closed nature of this or that Apple property.

I don’t know what all iPhone apps don’t exist today due to the restrictions imposed by the App Store, but I’m not sure I can think of an app right now that I’d rush to sideload. I’m sure there would be some, I’m just saying - it’s not a huge itch for me.

What’s becoming an itch, however, is the lack of a serious, native-like SDK for development of webapps. This solution has the following advantages:

  • Very, very open, from the standards defining it, to the engine implementing it, to Apple’s (current) stance regarding the web.
  • Web technologies are growing and improving rapidly - perhaps faster than any other computing platform today.
  • There are far more web developers in the world than Cocoa/Objective-C developers. If you’re interested in bringing the masses to iPhone development and vice versa, these are the masses. 
  • While web apps are far less powerful than native apps, note that 1) Apple can always choose to add JavaScript frameworks and APIs to match native functionality, and 2) sideloaded apps will also lack many features of native apps, such as managed updates, in-app sales, Game Center access, etc.
  • Pragmatically speaking, Apple would probably love to have a webapp SDK since they’re quickly becoming a huge webapp development shop - from iTunes to the App Store to apple.com to various native-app-embedded layouts (the Game Center in iPhone OS 4.0 looks like a web app.) This means it’s an itch they need to scratch for themselves.

There are many different ways the iPhone OS could become more open. Some folks won’t be happy until every single bit of tech in the darn thing is open-sourced, customizable, local, and organic. A mature webapp SDK would do the trick for me, and for many others.