I figured that you can create 2 workflows that are the exact same, both wait for and trigger each other after stop waiting.
WF: waiting for event 1
1) Enrollment trigger: Manual, enable re-enrollment
2) Delay until the event happens. 1825 days.
3) enroll in another workflow: waiting for event #2
WF: waiting for event #2
1) Enrollment trigger: Manual, enable re-enrollment
2) Delay until the event happens. 1825 days.
3) enroll in another workflow: waiting for event 1
Opinions?