The goal of this is that if there is a cryptanalytic attack that gives brute force a 2⁴⁰ speedup and hence attackers build custom hardware to implement it, their hardware is still not effective against the other cipher and they have to do something different (maybe hard to characterize how difficult the different thing would be anticipated to be).
If you're paranoid about AES, use Chapoly (or just use Chapoly because it's in many ways more convenient to use than AES). Don't build elaborate cascades (all cascades qualify), and don't randomize S-boxes.
It is hard enough getting these systems right when you're playing exactly by the book. If you're designing a cryptosystem and you're not a professional cryptographer, the list of things you should be worried about getting wrong is very long and very scary.
Serious question. I know nothing about crypto, just assumed "more is better, but slower".
AES-Serpent is probably not less safe than AES; it's just not necessarily as much more safe as you'd expect.
A much bigger concern than which precise ciphers you're using is which block cipher mode you're operating under; Truecrypt/Veracrypt uses XTS --- like most disk encryption --- which (among other things) isn't authenticated.
The funniest thing about TC/VC's cascades is that the keys are derived from passwords anyways: a giant clunking complicated block cipher cascade resting on top of a low-entry password secret. It's just a silly design.