I set up a RasPi exactly for the scenario you have in mind. Initial fill
(and maybe regular syncs of larger chunks of data) through USB and usual
access from windows through a samba share. SqueezePlug is definitely a
very good starting point for this.

Different character sets, however, caused significant problems for me.
If you are sure you don't have any umlauts everything might be fine
immediately, otherwise you will see funny names in windows for files
transferred through samba if you later connect the drive via usb - and
vice versa. Mounting with different characterset options, or playing
with samba config will solve the problem finally. But it is pretty
tedious ... 

I ended up using ntfs which can be handled by the pi as well.
Unfortunately I'm not a linux guy so I don't remember, what I exactly
did but there are lots of pointers in the internet -its a well known
problem. 

Just to make you aware of this potential issue. Of course, the easiest
way to solve this problem is to avoid umlauts completely, but sometimes
this is just not possible ....

G�nther


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