I have a whole lot of movies/tv shows I have purchased on iTunes or obtained digital copies of from physical purchases that I have not yet downloaded into my iTunes library due to lack of internal HD space (thus, each of the movies or tv shows has artwork available in My Movies and My TV Shows, but with the little cloud in the lower right corner indicating it is not localized yet). I bought a Drobo on which will be able to store all of the media and would like to place the movies and tv shows onto the Drobo but have it run through iTunes so I can centrally access it through iTunes. My question is this: do I need to download all of the movies/tv shows locally before putting it onto the Drobo or can I simply direct the folders to the Drobo (along with the currently downloaded media in those folders) and THEN have then download them from iTunes and have them save directly onto the Drobo? Essentially would future purchases and downloads be sent directly onto the Drobo or will I have to download them and then individually move downloaded files to the external drive? As I am likely dealing with a terabyte of content, I would really like to only have to do this once. Hence, asking before I do anything. Thanks in advance! P.S. I am thinking of using TuneSpan to send the folders over. I mention this in case this makes any difference in addressing my issue.