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Try forcing OS X to connect to your network share using SMB1 instead of SMB2. To do so: Open the Finder. Select Go -> Network. In the "Server Address" field, enter "cifs://yourservername" instead of "smb://yourservername".


I would set up a user to automatically log in and lock the screen immediately with a password (or as close to immediately as you care.) That will mount the external drive and start up sharin for all users. Alternatively, you could drop the $20 on OS X server and have it mount shares at boot like you rightly expect a server to behave.

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