I know the discussion has been centered around apps and such, but the first thing you want to do I'd get you contacts and calendars in order. With all the hassle, problems and everything else that came along with MobileMe, it has always worked well for me syncing between the iPhone, iPad and outlook on a PC.
Being able to enter or modify a contact or calendar item on the go, at my desk or on the couch and sync to everything else has been worth the 100 bux a month. Even better when it goes free.
I don't know the status of iCloud or what to expect when it becomes fully operation. In an ideal world with no storage or bandwidth limits, it could function exactly the same as contacts.
But for those who run into complexity issues syncing music and video via iTunes, will iCloud simplify the process, or add yet another layer of complexity?
My personal workflow, even though I don't keep up with it as someone else mentioned, is to use iTunes as the master, which is the only option for some things. I also try to update apps on the computer, then sync, but still find myself updating apps on the device first. I hope iCloud, at least when it comes to apps, let me update on a device then that would automatically update the app on the computer and the other devices, whether the app is made for both, or if the app is separate paid version.
I'm also finding more and more that a device offers more "master control" type options. For example, you can move an email message to another email account as easily as moving it to another folder as the same account. You can view calendar items from different accounts, say, from you personal account and an exchange account in one calendar view. But on the other hand, you can't create sub-folders on the device - you have to do that on the computer or web mail. And if you're using MobileMe, you can't log in there via the iPhone or iPad, thus, the computer is still part of the mix.
When it comes to organizing apps and folders, I finally decided it's easier to do on the device than in iTunes. Once past the initial stage of figuring out the categories and folder names, there's moving the app into the folder, which meant dragging it across several screens. However, I would temporarily remove the apps from bottom bar and using that as a staging area, much easier.