1 - You would do better to administer ClearOS remotely from your LAN with a browser by
https://Your_ClearOS_LAN_IP:81 rather than use the console directly.
2 - Again remotely, if you're using Windoze, grab yourself a copy of WinSCP with PuTTY. WinSCP gives you a graphical file manager and decent file editor and PuTTY gives you a console.
3 - I would have to check but it should almost work with Dump but I think you'll see an extra Dump folder in the menu tree because you are mounting sdc into /var/flexshare/shares/dump so folder sdc1/Dump will appear underneath this. It will look more confusing under the other two flexshares as they will both see folders User and Projects underneath /var/flexshare/shares/projects and /var/flexshare/shares/user. You may need to check out the "mount bind" command but I have little knowledge of it.
4 - The main reason for me jumping into this thread. If you have the subnet 192.168.1.x on both LAN and WAN you will not be able to contact your router from your LAN as the LAN will think all 192.168.1.x addresses are on its LAN. You should change your LAN subnet. Also another generally fundamental rule of these VPN's (there are exceptions) are that each end of the VPN is on a different LAN subnet. 192.168.1.x is very common in domestic routers so if you also have the same LAN subnet you will be able to connect the VPN bot no traffic will pass (possibly except if you do not allow split tunnelling and force all traffic through the VPN). They are both good reasons to change your LAN subnet to something different. Then the easiest thing to do is to set up the PPTP VPN to use a LAN range on the same subnet but outside the DHCP range.
5 - Under /home

and why bother redirecting them. Just allow the user to map them unless you specifically want to use a different disk. Even then you could mount a disk into /home (but move all the user folders first).