spec: rerun during paralleized_specs runtime and timeout fix

Change-Id: I8e50f989bcbbe762bb5d6d91243f81af1bf2de86
Reviewed-on: https://gerrit.instructure.com/32488
Reviewed-by: Bryan Madsen <bryan@instructure.com>
Product-Review: Bryan Madsen <bryan@instructure.com>
QA-Review: Bryan Madsen <bryan@instructure.com>
Tested-by: Jenkins <jenkins@instructure.com>