[taw20171030]

Not the OP and I don't use DO specifically, but I've found using a VPS provider to be a more or less painless VPN experience. Providers like DO, OVH, and Vultr have scripts for easy one-click OpenVPN setup, or you can roll your own if you don't trust their scripts (though if that's the case maybe you don't trust the VPS provider at all...)

That said, always verify that the tunnel is operating correctly before assuming it is and taking off. I've found on more than one instance that the OpenVPN client was misconfigured and seemed to connect, yet my IP was still being reported as my ISP's.

[unethical_ban]

I did notice the Vultr OpenVPN deploy has license restrictions of two clients.

[morganvachon]

I think that's an OpenVPN restriction, not a Vultr specific restriction. You have to pay for a commercial license if you want multiple connections with OpenVPN.