If you're interested, I explore that and related issues in one of my series on the IVPN website.[0] There's also an old guide on nesting VPNs and Tor with VMs.[1] And a tribute to Kevin Mitnick, featuring onion SSH hosts for chaining.[2]

The tl;dr is that compartmentalization is the key. At all levels. At physical levels such as hosts and VMs, LANs and vLANs, and uplinks and proxy chains. And at behavioral levels, such as interests, forums and social media, projects, and language and writing style.

Mirimir is my only main persona that writes about privacy issues. He has temporarily had a few secondary personas for particular projects, just for casual deniability. But none of my other personas have written at length in English.

0) https://www.ivpn.net/privacy-guides/online-privacy-through-o...

1) https://www.ivpn.net/privacy-guides/advanced-privacy-and-ano...

2) https://www.ivpn.net/privacy-guides/onion-ssh-hosts-for-logi...