Just a little update: I think I've figured out what causes autofs to stall.
Since I've tested sshfs and cifs, and reproduced it using both, I can rule out 
a specific target fs. 
I think it has something to do with the indirekt map feature:

#/etc/auto.master
/media/auto-smb/  program:/etc/auto.smb
/media/single-smb/  /etc/auto-single.smb

#/etc/auto.smb
#Same file as shipped with the Ubuntu package.

#/etc/auto-single.smb
* -fstype=cifs,vers=1.0,credentials=/etc/creds/myhost ://myhost/&

Every mount under /media/single-smb/ will automatically disappear after
$timeout. Whereas, a mount under /media/auto-smb/ will *not* disappear.

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https://bugs.launchpad.net/bugs/1754506

Title:
  AutoFS does not automatically umount SMB shares

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