Summary, your model is a little bit too constrained at first so the solver can't find a first solution.
AND, allow your super jobs to not be active in your method `add_super_job_constraints()`, i.e. `-1` aka not active
routing.VehicleVar(manager.NodeToIndex(jobs_assigned[key][num_addresses])).SetValues([-1, key])
e.g. for Day_Route_Feb26.pkl
...
Dropped nodes:
Route for vehicle 0:
31 Time(0,0) -> 1 Time(0,0) -> 24 Time(50,330) -> 16 Time(370,370) -> 10 Time(480,480) -> 31 Time(510,510)
Distance of the route: 139 m
Time of the route: 510 min
Route for vehicle 1:
32 Time(0,0) -> 9 Time(0,0) -> 17 Time(60,80) -> 29 Time(150,170) -> 4 Time(240,240) -> 28 Time(320,320) -> 30 Time(400,400) -> 2 Time(480,480) -> 32 Time(510,510)
Distance of the route: 123 m
Time of the route: 510 min
Route for vehicle 2:
33 Time(0,0) -> 3 Time(0,0) -> 27 Time(60,150) -> 19 Time(240,240) -> 21 Time(330,330) -> 20 Time(410,410) -> 5 Time(480,480) -> 33 Time(510,510)
Distance of the route: 92 m
Time of the route: 510 min
Route for vehicle 3:
34 Time(0,0) -> 0 Time(0,0) -> 23 Time(70,150) -> 26 Time(120,200) -> 25 Time(170,250) -> 18 Time(300,300) -> 13 Time(400,400) -> 8 Time(480,480) -> 34 Time(510,510)
Distance of the route: 119 m
Time of the route: 510 min
Route for vehicle 4:
35 Time(0,0) -> 6 Time(0,0) -> 11 Time(50,100) -> 15 Time(150,200) -> 7 Time(240,240) -> 12 Time(300,300) -> 14 Time(390,390) -> 22 Time(460,460) -> 35 Time(490,490)
Distance of the route: 96 m
Time of the route: 490 min
Total Distance of all routes: 569 m
Total Time of all routes: 2530 min
You can find the complete example.py in attachment (ed you must place your .pkl file in the same directory than example.py)