If you use the Pogoplug Drive application and your LAN is uncluttered (if local) or your internet access bandwidth is sufficient (if geographically dispersed) then it would seem that you can do both items you mentioned, and more.
The Pogoplug Drive is, in essence, just a mapped NetWork drive. MAC's I cannot speak; however, Windows allows files and executable to be used from mapped drive just as if they were on a locally attached drive (with some restrictions that only Microsoft Windows developers seem to understand).
Now, there are some software applications that object to using files on mapped network drives. Nothing in the documentation of most software gives any advise about these sorts of potential issues. Trial and mistake is the venue.
The concern of using a file or an executable, on a mapped drive, is the risk imposed by the "network" stability. If the network faulters there could be unrecoverable corruption. So, no biggie! We deal with uncertainty every day. Just make sure you have a "reliable" backup of any data. Make sure you are using an executable that will not do harm to itself should it get interrupted during execution (some keep profiles, setup files, initialization files, etc. that may not reset if the executable abnormally terminates which may require an install).
(NOTE: Many Windows software applications use the registery. Will mapped drive affect the necessary use of the registery? That is something that has to be tested. One never really knows what software developers really do with the code and what will actually happen if the software is used outside the intended working environment.)
If you are into linux, you have even greater options. Good luck. Just remember, you, and you alone, are responsible and in charge of your data and your executables.
Pogoplug Farming(tm) is Fun!

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