Why did they make this so difficult in doing?
They didn't make this difficult at all. People are trying to make it difficult by attempting to share iTunes Store accounts, Apple ID's, or iCloud accounts when that is not necessary at all.
I repeat, it makes no sense to share ANY account on your devices. Home Sharing takes care of that.
Yes, you can even share apps using Home Sharing. There's no need for sharing iTunes Store accounts. Especially in iOS6 since it no longer asks for the password when doing updates.
You will see people advise others to share iTunes Store accounts all the time but that is because this is how people used to do it before Home Sharing became possible and they never figured out how to do it with the better method that Home Sharing provides.
There are several downsides and loss of functionality when sharing iTunes Store accounts and it is completely unnecessary unless it is impossible to be on the same Wifi network as the person you want to share with.
For example, some things are attached to your iTunes Store account like your bookmarks in iBooks. Also if you share iTunes Store accounts, it means you won't be able to take advantage of the automatic downloads feature. There are other limitations and possibly more coming in the future. Use Home Sharing instead.
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So I have been able to get by with one Apple Account for myself used on my MBP, my wifes MB, her iPad and her iPhone. This Fall I plan on purchasing an iPhone for myself and I'm thinking that for calendar and other personal preferences and in light of the apps I have purchased, I'm wondering after establishing an Apple Account for my wife, what is the best way for me to get the apps purchased on my account over to her device? I'm hoping they don't have to be purchased again.
Any suggestions or strategies appreciated. Thanks!
It is very simple. Stop sharing
any accounts. Use your own Apple ID, iCloud accounts, and iTunes store accounts. Start using Home Sharing. Problem solved. As long as you are able to be on the same Wifi, that is the best way to handle it and it is the approved way to share apps, music, movies, tv shows, and other purchased content amongst your family without repurchasing.
Doing it this way is also the simplest method. You only need one Apple ID. When you set up your new phone, you just put in that one Apple ID and everything is setup automatically. You don't have to go into the Store settings and change anything. And your wife only has to use her one Apple ID.
The advice you've been given in this thread is not really the best way to do it. It used to be but it is not necessary anymore and Home Sharing is a better way.