I have the $99 plan. The one problem I have is that one of my computers has an SSD so I can't move more stuff to Dropbox on my desktop because it would kill my laptop, which is the reason I bought it. I do much of my work on my laptop out of my Dropbox dir. With so much Dropbox space, now I don't want every computer to have all my pics, videos, etc.
I guess it will. I bought Dropbox one morning in a panic when I thought my drive was dying. It turned out to be fine but I've been working out of the directory since then. Thanks.