Many people are not simply paying for an encrypted connection, they're mainly paying for a) an IP that cannot be easily attributed back to them, and b) a large garbage can for DMCA complaints.

The Raspberry Pi provides neither of those, and requires occasional maintenance.

1) PIA is less than $35 a year

2) PIA takes less than a minute to setup on every device. Download the app, login, and you pretty much never have to worry about it again.

Your alternative is more expensive, more resource-hungry, and more of a pain in the ass.

there are a pretty large number of commercial openvpn service providers, that if you pay for 1 or 2 years of service, the cost will range from $2.80/month to $5.50/month. I would be surprised to pay $10/month. I have my own OpenVPN endpoint for testing which exists on a $5/month VPS, but it has a 2TB/month transfer quota, while many commercial openvpn service providers have no transfer quota per month.

Ideally you want to have both, if you move a lot of vpn traffic (cough cough, 4k HEVC torrented things), you can have your own openvpn setup on a KVM VPS you fully control with root, and also a commercial $3/mo openvpn service where you won't run into a 1 or 2TB/mo limitation.

here's the pricing for a fairly normal commercial openvpn service provider:

https://www.purevpn.com/order

This is like the comment on the Dropbox thread when it launched. "Why would I pay for this when I can [insert 5-step process here that is not at all easy for the vast majority of population]?"

Am I the only one that does both? I use OpenVPN to connect from my remote devices to my home router. My home router then uses an OpenVPN tunnel to PIA for all Internet bound traffic.

For those saying that anyone setting this up at home doesn't value their time, my router has built-in support for OpenVPN in both server and client mode. The VPN connectivity and tunnel to PIA took me about 15 minutes to configure a couple of years ago and besides having to update the PIA password has required no real maintenance.

For many, I'm sure they feel their time and/or convenience is worth more than the price difference. It doesn't take a ton of time, but it's enough of a time/effort that I don't think it's wrong to assume that many just want to sign up for a service and have it work instead of building their own.

This suggestion assumes time has a cost of zero. Not to mention, some solid VPN services (Mullvad) can be had much less than $100/year.

That said, it could be a fun project regardless.

Can you elaborate on this setup? A portable VPN server, is that correct? You have a Pi that has openvpn installed and you connect to the Pi? Do you have issues with captive portals example the coffee shop or hotels?

Who is going to host the Raspberry Pi, and do they guarantee they're not keeping connection logs?

If the Raspberry Pi is in your house then any site you visit (or any frames they embed or other resources they load) can still track you by IP.