Jon, I am not sure I understand exactly your home setup but here is what I do. I organize my files by year and the present year I keep in a Dropbox folder and I subscribe to the 100 GB service. I have 3500 images (D300 raw) thus far this year which are continuously backed-up wirelessly. My macbook pro harddrive and and my older images on an external harddrive are backed up by Crashplan. Thus the MacBook harddrive is backed up continuously wirelessly. I also daily connect my MacBook to a Time Machine external drive. Thus I am constantly backing up my images to 2 places in the cloud and on a daily basis a 3rd copy is being backed up to Time Machine.