No matter what chart software you end up using, the situational awareness that the iPad will give you is priceless. I was used to Jepp binders as well from the 121 world, but I've gotten used to the new plates on the iPad. Let me tell you, when you see your little blue airplane flying around on the approach plate view, and driving down the taxiway on your 10-9 chart, you'll grin every time. In regards to the arrival and approach plate not showing together on the iPad, there is some truth to that (at least with ForeFlight) but rarely is an issue. The Seavu arrival into LAX came to mind when I first read that, as I remembered how fixes on the end of the arrival to ILS25L (for example) overlapped onto the approach plate for 25L (Jepp paper). And also with Foreflight, I found it odd that the SIDs and STARs were the only display that doesn't show the little aircraft icon moving along the airway. Where as all the High Enroutes, approach plates and taxi diagrams show your jet trucking right along.
And with anything digital, just get used to having them fully charged all the time. The geo-positioning feature hits the battery pretty hard, and you may or may not have an AC Charger plug in your cockpit. I personally am an Apple fan, but as anyone here with at least an iPhone knows, sometimes they freeze up and requite the "hard reset." I have had an iPad act up once or twice up there, but nothing limiting. Someone mentioned it above, but it is easy to print off the charts, which I have done on occasion in crazy-busy environments just in case.