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What about when you need to update the box? How does it handle protecting and maintaining the vm? What if there is a critical vulnerability in either the client or the server, how will you find out?

I know i'm capable of running my own VPN, but I'd rather pay someone else to manage the details and I just get an endpoint I can connect to that will always work (and will be shut off if there is a major security problem).

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unattended-upgrades is enabled by default, so security updates are handled automatically. You can also just destroy and recreate the box once in a while, without any extra cost.

But it is of course completely up to you. If you trust your VPN provider when they say they don't log anything, I guess you are fine.

If you want a VPN so that your activity is not logged, how will hosting your own under your own digital ocean account help you?

Sure, your activities may no longer be logged, but does that matter when 100% if the traffic coming from your droplet IP must be yours?

This is definitely a valid point. In my case, I share my VPN with friends and family, and also use it from a number of different devices (several laptops, and mobile devices). Anyway, the point is not necessarily to make it impossible for anyone to connect my internet traffic to me, but rather make it harder to monitor me.

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