This is what I know:

1 - User Friendly is relative to what background you are coming from. I am not familiar with Azure. It sounds like you may be the Project Manager. I have used both Jira and Asana. I think Jira feels and looks more simple. Jira is more Project and software-dev oriented. Asana is more general, not to say it isn't designed to handle a development project. I think your decision is going to come down to: *Who is currently using what? *How is it going to be to get the individual outliers to adopt a new management style? Some will adapt and some will refuse. 2 - I believe they all have a level of automation 3 - I know Asana will let you tag and prioritize. Jira will allow you to prioritize, tag, make teams, and separate the projects by teams if you like. 4 - Again you can create teams and you can control the team visibility to projects. 5 - I know Jira will allow you to create a human resource with a burndown. 6 - Jira can assign tasks, projects, etc. to individual team members. 7 - With Jira comes Confluence. Here you can keep lots of support documentation. They have lots of templates that can be used as well. 8 - Jira does allow a lot of integration. It is designed for Product and Project management of HR and Software. If software devs didn't see a robust integration feature they would be very disappointed.

My Stack

Application and Data

Utilities

DevOps

Business Tools