A:Answer All new software. The Apple operating system is iOS. The Android operating system is ... well, Android (it's a Google thing). In general, they don't like each other, they don't talk to each other, and they even have separate app stores.
The good news is that Microsoft Office files (Word, Excel, etc.) and PDF files stored in your cloud account can usually be downloaded and opened by the corresponding app in either operating system. So ... barring any fancy features not supported on the new operating system's version of the software (i.e., the app) ... you should be able to download the corresponding app to the new Apple (from the iTunes store) and then pull your old files down from your cloud account. The store's tech support people can walk you through this PDQ (though they want a small fee).
ALSO, if you want to print to your printer without a huge amount of hassle, make sure it has something called Airprint. Your new iPad / iPhone / iWhatever uses Airprint to talk directly to the printer with a minimum of hassles. If you are thinking of replacing your printer, make sure it has Airprint.
I see you mentioned WebRoot. Please call them before downloading anything. Some of their products are iOS-compatible. Some are NOT! Take note that "MAC" compatibility is NOT "iOS" compatibility (because Apple maintains these two operating systems as two completely different products with very little interconnectivity).
