A user can buy Apple's entire collection of iPad apps (Pages, Numbers, Keynote, iPhoto, iMovie, and GarageBand) for less than the cost of Omni's task manager, OmniFocus.
Yes, but Omni have to make all of their money from software sales. Apple can use software as a "loss leader" to promote the sale of iDevices and Macs.
I agree that Apple need to remember that not all vendors can make money that way, and that they can't push the price of software too low.
Apple responded with IAPs, which I think most of us feel is monetizing at too small a level and is having a detrimental impact on App quality.
IAP isn't just for smurfberries.
Offer a free update with the same functionality as the original and sell an unlock code for the new goodies as an IAP. That way, everybody gets free bug- and OS-version-compatibility fixes for free, and the vendor gets a chance to really plug the update. I suspect the uptake rate would be pretty high...
Demos could be handled in the same way.
This is pretty common on Android - not sure I've seen it done on iOS so much, but technically it is no different to what games with IAP do.
Apple responded by never pushing new major versions of those Apps.
See above: from Apple's POV, income from software is nice but their software mainly exists to sell hardware.
When talking about App Store prices, one thing to factor in is that App Store purchases are licensed for all the machines you use (OK, no OSX-to-iOS cross-licensing, but in general OSX and iOS apps are completely different entities). Outside of the store, many vendors still expect you to buy one copy per machine, sometimes enforced by DRM.