So I'm running a windows machine with a paid for by BTC VPN, then I have whonix running in Oracle VM with a VPN after my Tor connection for safe browsing.
Note that I can't access onions at the end of it all, only with the last VPN turned off.
But say I was doing illegal things on the clearnet, at the end of the VPN > Whonix > Tor > VPN, is there much of a chance of being able to be 'tracked'?
If you're still using Windows, yes.
tl;dr -- if LE wants you, they'll get you