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I used to jailbreak for a few things. eg on my 3GS to get a hotspot I needed MyWi, and I wanted Intelliscreen. Once I moved to a 4S, and got iOS7, all those needs were eliminated. I jailbroke on my first iPhone because it wasn't being sold in Australia and without a jailbreak, it would not be usable. I've lost interest since Cydia has become so commercialised (not that I think those people don't deserve $$$ compensation for their work, they do), and I don't think my 4S can be jailbroken anyway, now.
Havent bothered with jailbreaking ipads since ipad1.
I rarely want to use the device as a file storage thing, but there are plenty of apps on the app store which allow that. The first one I had was called Data Briefcase (or similar)... its no longer being developed... As for using files with multiple apps... dropbox. Not sure what else you'd need to be doing.
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