Dynamic OpenVPN Network with multiple droplets and configurations

Hi there,

The short version:

Is it possible to have dynamic OpenVPN configurations based on the client profile that is connected to it?

The long version:

I was able to successfully set up an OpenVPN server on Ubuntu 16.04 with the help of this awesome tutorial: https://www.digitalocean.com/community/tutorials/how-to-set-up-an-openvpn-server-on-ubuntu-16-04

I have been using the VPN service with my computer since a couple of days and everything works amazingly well. I am still relatively new to the VPN server world, but I would like to try to improve the setup for my private use.

I followed this tutorial below to set up Pi Hole for DNS based Ad blocking: https://www.cyberciti.biz/faq/ubuntu-linux-install-pi-hole-with-a-openvpn/

This worked also without many issues, almost too well. However, sometimes I would not like to use it. Then I usually connect via SSH and change the DNS “dhcp-option” lines back to Google’s nameservers. This was the first time when I wondered if I could control the OpenVPN configuration based on the client profile that is connected to it? In best case I would have two profiles that utilize different OpenVPN configurations. Is this possible?

Secondly, due to my local internet connection, I noticed that the connection between my computer and the VPN (in another country) is sometimes very slow. It would be amazing if I could create a droplet in a region closer to my location, essentially resulting in this set up.

My computer -> VPN Connection -> Droplet 1 (close to my region) -> VPN Connection -> Droplet 2 (in target region) -> Default or VPN Connection -> Target Service

I assume that I could set up a OpenVPN server and client in Droplet 1 running at the same time. That would create a network as outlined above. But again I have the big question, if I could create multiple client profiles and depending with which profile I connect, I could control if I use the network as outlined above or maybe directly connect with Droplet 1 to the target service. Essentially is it possible to have dynamic OpenVPN configurations based on the client profile that is connected to the service?

With my beginner knowledge, I read that Tinc supports multiple nodes easily, but at the same time many users seem to prefer OpenVPN over Tinc.

In case it is relevant, I come from a web development background (PHP,JavaScript,etc.), but I also know my way around in bash scripting, Java and C++.

Any help, even just links that help me to better understand the possibilities.

Thank you,

Jan