The problem is that curl|bash isn't authenticated, I don't really know whether the executable I'm getting was really built by the maintainer or if a malicious attacker was able to sneak in and replace it (like what happened with eslint a few weeks ago[1]). Passing off a signed package (as .debs are) as genuine requires getting a hold of the signing key as well, which increases the difficulty of the compromise.
No, it doesn't. We're not talking about the Debian package archive.
We're realistically talking about the hypothetical where a .deb is sitting on pi-hole.net, with a GnuPG key right next to it and instructions to trust this key.
[1]https://eslint.org/blog/2018/07/postmortem-for-malicious-pac...