Hi @Tim Robbins,
Sorry about the late reply here. I can see how the current impersonation flow would be painful if you were having to do that many times. We're currently in the process of reviewing that design decision to force a logout. We plan to implement a better flow in the coming weeks.
As for where you end up after impersonation, it's based on where you're triggering impersonation from. The redirect URL is recorded from where you began the impersonation from. Unfortunately, we cannot check your ability to reach where the impersonated user would go during the impersonation process. The orange 'wheel' at the top left corner will always take you back to the 'home' page where you can see what's accessible by the impersonated user. The drop-down menu in the navigation bar can also help you reach a different apptio endpoint.
Hope that helps!
Thanks!