We have a file share in our small office (3-5 users). We now have the need for the files to be accessible outside of the office.

I like the idea of dropbox - we have been using it for small remote sharing. If we buy the upgrade account, and move 30 to 70 gigs of files to it, will every user have to have the pro account?

I have submitted this question to dropbox - but thought that the advice of users here would also be valuable

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This question from the Dropbox FAQ suggests that every user will need a pro account to access a shared folder that's larger than 2GB. You may want to consider other online file sharing services to see if they fit your needs. (At first glance, it looks like Drop.io, the first option listed, may be exactly what you need.)

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