Escalation Rules

Summary

Multiple Escalations not working

Content

I have a question about setting up rules.
I have a series of rules that we use for escalation. They all work individually, however it i have a case where an incident is escalated under 1 rule, then the escalation removed, I can't get it to escalate again under a different situation.

I've attached a document with my rules spelled out and different scenarios. These rules are just in our system as tests, so that is why i am using a 5 minute time frame and only looking at incidents with "Dave" in the subject.

if someone can give me guidance on what i need to do to fix my problem, that would be great.