Chocolatey vs Yarn
When comparing Chocolatey vs Yarn, the Slant community recommends Chocolatey for most people. In the question“What are the best Windows package managers?” Chocolatey is ranked 2nd while Yarn is ranked 10th. The most important reason people chose Chocolatey is:
Chocolatey has a massive community package repository of installs (more than 4,000 packages), and its open nature allows everyone to contribute more as needed.
Ranked in these QuestionsQuestion Ranking
Pros
Pro Large number of applications/utilities available
Chocolatey has a massive community package repository of installs (more than 4,000 packages), and its open nature allows everyone to contribute more as needed.
Pro Sieg
Installs silently without crapware.
Pro Easy to use
Just open powershell and type choco install firefox
to install Firefox, or choco install java
to install Java.
Pro Straightforward install process
To install Chocolatey simply copy the text from their site and paste it into either cmd.exe or powershell.
Pro Upgrade all software with one command
choco upgrade all
is like Windows Update for all of your 3rd party software. ... or for the more succinct command use 'cup' !!
Pro Downloaded files are verified by checksums
Chocolatey requires checksums by default for files downloaded over non-secure locations and highly recommends it for HTTPS/SSL locations. It is moving towards requiring checkums by default for downloading from secure locations.
Pro Manages the entire software lifecycle
From install to upgrade to uninstall, Chocolatey manages the whole process.
Pro Scriptable
You can put Chocolatey install commands into your powershell scripts.

Pro Free and open source
It's licensed under Apache License 2.0 with source code available on GitHub.
Pro Decentralized package sources
Packages can be installed from multiple sources, including private sources.
Pro Builds on technologies you know
Unattended installation and PowerShell.
Pro GUI available
There's a package called ChocolateyGUI that can be installed and lets you use Chocolatey with a UI frontend.
Pro Integrates with almost every configuration management / infrastructure automation / RMM tool
Chocolatey integrates with almost every infrastructure automation tool out there.
Pro Support and features available for organizations
There is a business edition available for organizations that need more support. The business edition also includes a Package Synchronizer, Package Internalizer, Package Builder, and a host of other features.
Pro Can be extended with PowerShell
Chocolatey allows installing extension packages that add PowerShell functions to your package automation scripts.
Pro More Selection
It has programs that can't be found in scoop or ninite.
Pro Custom sources
It has ability to add custom sources.

Pro The same results will be yielded every time yarn is run in a repository
One of the most important aspects of Yarn is determinism (predictability). The lock file ensures that the same dependencies will always be installed in the same way and order regardless of the machine for a given repository.
Pro Can tell you why a package was installed
yarn why <query>
can tell you why a package was installed and what other packages depend on it.

Pro Good network performance
Yarn efficiently queues up requests and avoids request waterfalls in order to maximize network utilization.

Pro Offline mode
If you've installed a package before, you can install it again without any internet connection.

Pro Flat Mode
Resolve mismatching versions of dependencies to a single version to avoid creating duplicates.

Pro Multiple registries
Install any package from either npm or Bower and keep your package workflow the same.

Pro Network resilience
A single request failing won't cause an install to fail. Requests are retried upon failure.

Pro Good documentation
It looks like it has good documentation.
Pro Security is put at the forefront
Even though it's still in its early stages of development, security is one of the core values on which Yarn is built. It uses checksums to verify the integrity of every package before executing its code. This also helps avoiding errors related to faulty caching or captive portals.
Further steps are also being taken to improve the security of Yarn which will be implemented in the future.
Pro Built by the community for the community
Even though it's backed by Facebook, Yarn is built as a community project first and foremost. It's completely open source and hosted on Github. It's released under a standard open source client and has its own GitHub organization and set up to work under the same governance model that other successful projects have used in the past, such as Rust and Ember.
All of this means that both existing and new contributors will always work together to improve the product and introduce new features while also keeping in mind suggestions coming from the community.

Pro Backed by Facebook and Google
Was created in a collaboration of Facebook with Exponent, Google and Tilde.
Cons
Con Sometimes hard to know which package to install from community package repository
The community repository contains multiple packages with similar names, making it hard to know which one to install. This is of course only related to using Chocolatey with the community repository, and you can look up the number of downloads to see which are the most widely used.
Con Some package installs aren't good or polished or don't install well
Macrium downloads the online installer, 7-zip doesn't associate files, PotPlayer is outdated, etc.
Con Unable to easily change your install directory in the free version
In the free version you must know the native installer switches and pass them through with install args. In the paid versions you have a ubiquitous install directory option where Chocolatey determines how to properly pass that to the underlying native installer.
Con Buggy
Slow, many packages fail to install, and config can corrupt causing it to not be able to manage packages anymore, leading to a bunch of installed and non-updateable software
Con Incomplete and conflicting package options
Not enough maintenance done to package library so there are different similarly-named or -versioned packages available, some broken and some not.
Con Can not download asynchronously
Con No support for ARM64
Users with Windows on Arm can't install native ARM64 binaries. Apps installed with Chocolatey run slower and need more resources on Windows on Arm because they have to be emulated.
Con Uploading packages can be time consuming
It can take weeks to have a package accepted and with a fair amount of resubmitting for the dev/ maintainer.
Con Doesn't care about supporting the community
They used the community to make it the largest repository of packages. Now that they're the de facto standard package manager, they only care to support those that pay them and refuse to fix problems with popular packages.
Con Takes up disk space
Yarn adds to your disk space usage since it stores dependencies locally.
