There's an 80/20 thing here, though. Except more like 99.9/.1.
Yes, there is value in ensuring software is delivered without tampering direct from a trusted source. But the main problem people are dealing with is finding a trusted source for the install - one that actually delivers the software they wanted, without malware, without a confusing installer. Chocolatey solves the main problem pretty well. I can look at download counts, comments, and repos to verify what the installer is doing. There's an active forum that discusses problems or suggested improvements to packages.
It doesn't verify that there's no tampering along the way, but for most users that's an absolutely miniscule problem compared with the "Google / Click Link / Install Wrong Program and/or Malware" system.
While that's a nice sentiment, it indicates a rather complete lack of understanding of security issues by chocolatey in the first place.
Sure, they can move that particular download to https, but it doesn't install any confidence that they've thought through the rest of their flow. As far as I can tell, packages don't even need to be signed.
As a result, I'd not be able to trust anything they do.
I can
cinst putty
and get what I need automatically.
Sure, I have to trust the maintainer, but you know, if more people used Chocolatey to install packages, more people might be able to ensure it's safe.
It's not bulletproof but it sure is better than searching the web for the right download.