So I've set and tested the link between my Chromebook and my OpenVPN server and it seems working flawlessly but Murphy got me again.
It looks that when bridging is invloved OpenVPN failing to create tun0 device and outputs "connot find device "tun0" ".
When both devices on the same lan it will work fine as there's no need for bridging.
The solution for this is to manually create 2 tun devices: tun0 and tun1, this will force OpenVPN to create and use tun2 which will work flawlessly.
$this->bbcode_second_pass_code('', '# ip tuntap add tun0 mode tun
# ip tuntap add tun1 mode tun')