It's been just about two years since I upgraded from a Samsung flip phone to the Blackberry Storm2. In those two years, I have not been impressed by the Storm2 or Blackberry in general. It's about time I upgraded again. I've been looking at the iPhone 5 (or even the 4S if it's still available closer to Christmas), but I have some reservations about the new lightening connector (I already have several iHomes and other peripherals for my iPod) and the complaints about increased data usage. I do like that even the new iPhone 5 will connect via USB to my older Macbook running Snow Leopard 10.6.8. I'm pretty tied to Google for gmail and other things (I also like using Google Maps and Sync on the Blackberry), so I'm not ruling out Android as a possibility. I'm on Verizon with no plans to change networks, so that does limit my availability of certain Android phones (I'm opposed to jailbreaking since I'm not incredibly tech savvy). Having played around in the Verizon Store, I can say that I'm not a huge fan of the size of the S3. I prefer the Motorola Droid Razr M in terms of size, but my dad just traded in his original Droid for an iPhone 4S with a long list of complaints about Droid, especially as it aged. I like longevity, even if that's hard to come by with smartphones. My Samsung flip phone lasted for 5 years with only minor issues during the last 6 months of its life. The Blackberry started having issues after 6 months. I'd like something that could at least last through the 2 year contract. My question is about the compatibility of Android phones with a slightly older Macbook. I like being able to backup my phone via USB and being able to load my iTunes music. Is it even possible to backup an Android phone on a Macbook? If not, is there a system similar to iCloud? I've become pretty used to Google Sync for my calendar for a few months when Blackberry didn't support any Mac OS after Leopard 10.5. Basically, can I make an Android work in my Apple world like I made the Blackberry work, or is it time to completely embrace Apple and the iPhone?