Thanks for the suggestions Jamie!
What I ended up doing was create a condition checking for the CurrentAssignedAnalyst != Null, then routed any assignments after "In Progress" status to an "Add Assignment" action, then check for that condition, if null, send to "Awaiting Response" status, otherwise back to "In Progress". Works like a charm
import System
static def GetAttributeValue(Incident):
Value = false
if Incident._CurrentAssignedAnalyst != null:
value = true
return Value
