Outline looks interesting. At first glance, it looks to be targeted at news organizations with dedicated IT staff.

Speaking of DigitalOcean, I ran across a blog entry with a how-to on installing pfSense on a Droplet.https://squigly.blogspot.com/2018/02/running-pfsense-on-digitalocean-droplet.html

I have a pfSense router in my basement, with IPSEC tunnels up to a couple of other pfSense boxes, so the prospect of having a tunnel to a DO Droplet is interesting.

I have my pfSense box setup to be an OpenVPN server, and I connect to it with phablet/laptop if I’m on someone else’s wifi. (for that matter, my wifi access point has no access to my LAN; WANs only — like a DMZ but not Internet-public — so I have to VPN in on any wifi).

I also have it running as a DNS resolver, so my DNS queries are not going to my ISP (or an alternate DNS resolver)

If you are looking to run your own VPN server so you can connect to the Internet via your home ISP when you are in a coffee shop, take a look at pfSense. It’s free, and can convert any low powered intel PC into a decent firewall. It has a good implementation of OpenVPN and there’s a package available (openvpn client export) that makes setting up Open VPN clients, each with their own username/pw plus a generated TLS cert easy (and you really should use both cert and pw to secure your connection if there’s anything on your LAN you care about.