[nostril]

I think if you're interfacing with your server without going through Whonix, you're asking for trouble. Not only do you need to pay for the server using BTC that can't be traced back to your identity, but anything that touches the server (such as your server you're proxying with) needs to take the same precautions, which means no DigitalOcean, unless you can somehow pay them without that also being tied to your identity.

If you're not actually worried that DMCA people will follow through on their threat to sue you, or you really want to risk losing your property in the event of a lawsuit, then perhaps this might work.

Feel free to email me for more advice or to keep in touch. Your project sounds interesting.