I'll briefly explain what i would like to achieve whitout boring anyone

First of all, i'm not an expert and i have just started to get my hands on this stuff...
I am trying to connect to a Server (Windows Server 2016) trough a VPN and then make this Server connect to a Commercial VPN (PrivateVPN, NordVPN, PrivateTunnel). Is it possible?
I didn't try to install openVPN Access Server as i wanted to try a simpler solution first, but after creating successfully the first connection (client > server) when i try to make the second connection (server > vpn) the server just crashes and i have used PrivateVPN and PrivateTunnel, both with no results.
Basically what i want to do is: client > server (vpn) > commercial vpn > Internet
So when i surf the web using my PC my IP address is going to be the Commercial's IP. Is this possible?
Would openVPN help me or i'm missing some settings in my server?
Thank you in advance.