How do I keep my "iDevies" in Sync

Hello everybody,
     I realize this sounds like a question I shouldn't have to ask, but surprisingly I have not been able to figure out the answer on my own yet. Hopefully there is a simple solution or a step I missed somewhere but I just got an iPad a few days ago and am still trying to get everything setup correctly.
I started it by restoring a backup from my iPhone which seemed to get me where I needed to be, at least the majority of stuff copied over. The desktop and icon layout didn't transfer but all the apps I tried seemed to have all their data so I thought I was in business. I noticed pretty quickly the app I use to keep track of my spending did not stay in sync with my phone but I thought that might have been an isolated issue and figured maybe there was just a better application I could get but now I'm noticing other things are also not syncing. Obviously my finances are significantly more important than game data and I am willing to download new apps where necessary if anybody has a suggestion but what I need if for the changes on one device to be reflected on the other. If I download an application if automatically shows up on the other, but the associated data does not. I thought it might be a simple issue of plugging them in and syncing but that does not seem to copy the information over, unless there is a setting somewhere I missed?
For example the two main things I've noticed so far are the Accounts - Checkbook app from SVT Software (This one is important) and Hill Climb Racing. The bank account app I can replace if I have to, that one I would really prefer to update live if possible but if I don't need to it would obviously be easiest to make what I have already been using work. As for the games and other stuff this less important of course but if I spend all day stuck at the airport playing hill climb on one thing I don't want to have to do all that work again on the other to get back to where I was you know. I also thought my pictures would copy over but only the new stuff seems to be going to My Photostream, I would really like everything to. Hopefully I don't have to copy them all manually?
Thanks for your help everybody.

deggie covered a few points, so I will not rehash those.
As for your photos in Photo Stream - only photos that you take moving forward - after Photo Stream was activated on the iPad - will sync to and from the iPad. It does not work with photos that were already on the device before Photo Stream was turned on. Yes, those photos will have to be transferred manually if you want all of the same photos on both devices. Any synced photos from iTunes can be synced to the iPad. There are third party WiFi transfer apps that will let you send the older photos from the phone to the iPad.
I use this app for WiFi photo transfer.
Wireless Transfer App Easily send photos to iPhone/iPad ...

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