I’m familiar with chocolatey but AFAIK, WSL requires a reboot to be fully enabled.
Also, bootstrapping WSL or Cygwin is taking time on your test run. I do bootstrap cygwin+ansible in appveyor currently and lose 10min on each run.
There are also other considerations like mentioned here.
powershell script creating certificates with openssl not working under travis/git-bash but it does in appveyor
For now, I’m waiting on better support of direct powershell to continue my testing of travis/windows