The short answer here is that OS X is an excellent platform for running 
services, but really lousy for graphical user interfaces for said services.  
This ought to be regarded for the failure that it is by some Mac users, but 
seemingly isn't, for some reason ...

Depending on your needs, and if network conditions are favourable, in your 
situation I would set up PureFTPD with virtual users to implement the solution 
that you're looking for.  There was a cocoa app called "PureFTPD manager", but 
it hasn't been touched in quite a while, by the looks of it.  Still, this 
cannot be a trivial operation; you need to understand the command line and the 
wandering ways of Unix in order to get, compile, install and configure the 
server program.  I do not believe the included FTP daemon, tnftpd, can help 
you; it doesn't support virtual users.

I recently came across a nice app in the MAS called "Simple HTTP Server Pro".  
Perhaps, if you don't mind being logged in all the time and binding to 
unprivileged ports above 1024, you could do it using HTTP and WebDAV, which is 
easier to pass through NAT.  But this app only supports one set of 
authentication credentials, by the looks of it, so it isn't a complete solution.

So in short, I'm afraid this will be an in-depth challenge for you.  Nothing 
can substitute for the vertical graphical servers found on Windows.  Still, if 
you fancy a challenge, go for it.

As to OS X Server, I believe there are good reasons to use it irrespective of 
the file sharing services, such as the Caching service, but as far as I can see 
the file sharing support in there would not be of any help to you unless you 
particularly enjoyed exposing AFP or SMB over the Internet.  It could be done, 
I suppose, if you had the gall, but you'd have to be very careful, and I'm just 
not sure it's worth the risk.  Many networks in fact block at least SMB, so 
you'd be losing your Windows sharers, without a VPN.  And NAS products on the 
market (including, ironically, Apple's own Time Capsule) might be a better 
choice for doing that anyway.

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