Mail For Kindle
Info about the .mobi file format can be found here
More information here (Quite detailed).
Also … here
IDEA
Why not use the iPhone as a payment method. i.e. buying the app gives you access to a service - nothing more.
Use the source code of Calibre.
GAE based ?
Is iOS the best platform to go with? Not sure but it does provide us with an easy payment method. If we go primarily web based then can port to Android / WebOS.