Always be going through at least a burner VPN purchased with prepaid-card(bought with cash) or bitcoin.
I'd still recommend connecting to a box you can scrap, again, purchased anonymously, or 'found'(but not by an IP associated with you unless you plan to scrap it) before routing traffic through TOR.
generally:
-Don't keep old boxes.
-Don't save shit you don't need, ever.
-Don't do anything 'bad' from home or work, if absolutely necessary to be done in those locations use cash bought 3G.
-Additional layers does not help if you can't add them with assured anonymity. If a box has been touched by anything that can trace back to yourself, it's dirty.
Lastly, by 'illegal' things I mean leaking information that could get you killed, purchasing substances that are currently illegal, generally interfacing with the internet anonymously.
If you're a pedo, get help; if you're producing pedo-porn, consider suicide.