I'm in the market for a new "setup." Currently I've been using a 13" cMBP for about two years now and I'm ready to buy something new. I have always envied the 15" users for their roomier screens and nicer speakers. However, as I used my 13" in college I enjoyed the portability and small form factor. I am planning to return to school in about a years time so I do want something I can still tote around campus. But, I also want something with a larger screen. So, I'm thinking about buying an iMac and a 13" Retina MBP. Or, a 15" rMBP and calling it a day. My questions to you are whether or not you prefer one machine or if two machines has worked out better for you. I've never owned more than one computer. Is it a pain to maintain two machines? Is it a hassle to transfer files and data from one to another? Also, what about backing up files in the cloud, can I back up files from the iMac and the MBP to the same iCloud storage file? Lots of NOOB questions so I apologize in advance. Thanks for your input!