I will concede that Ansible does not have the best error messages. I've been working with it for a few years now, and knowing the true source of the errors has

I will concede that Ansible does not have the best error messages. I've been working with it for a few years now, and knowing the true source of the errors has taken a while just because they're not always very straightforward. That being said, there's lots of smart folks on the IRC channel that are always willing to help. I think the biggest advantage (in your case), is Ansible's idempotent nature. It takes way more work to make your shell script idempotent that it does writing a playbook for the same thing. I'm also curious about your current dev environments. Do you call Ansible through Vagrant or are you using completely Ansible to spin everything up? Getting the runtime environment installed/configured correctly can sometimes be a challenge for people just starting out (it was challenging for me at least) and if you have 10s/100s of engineers trying to set up Ansible properly and run playbooks themselves, you may have a bad time.