I don't want to hate on chocolately too much, because it has filled a very obvious gap in the Windows landscape for so long, but I really don't like it.
The biggest problem is that there are invariably 5 different packages for anything you want to install, with no reliable way of deciding which is the real/main one.
Another problem is packages constantly breaking. This can happen because packages actually pull files from remote, primary sources, and those files disappear or the site goes down, but also for a myriad of other reasons.
Yet another problem is the reliability of the chocolately site - it seems to go down or be slow as hell quite frequently.
Another gripe is that AFAIK, chocolately doesn't support 3rd party repos.
And finally (and this one is totally subjective) the website is ugly.
So as glad as I am that chocolately filled a void, I'll also be glad for Microsoft to provide an official, reliable replacement that also supports 3rd party repos.