First you need to create a dictionary. Keys are unique, if you want to store multiple values under one key, store a list as value. Then draw from it:
tasktotal = ["Medbay/Submit Scan","Medbay/Submit Example","Cafeteria/Connect Wire",
             "Electrical/Connect Wire","Cafeteria/Empty Garbage",
             "Security/Connect Wire","Navigation/Navigate",
             "Upper Engine/Fuel","Lower Engine/Fuel","Shield/Prime Shield",
             "Storage/Empty Garbage","Admin/Swipe Card","Weapon/Clear Asteroid",
             "Admin/Connect Wire","Storage/Connect Wire"]
# import defaultdict
# d = defaultdict(list) 
# instead of d={} and then simply use d[key].append(...) it creates
# the list itself
data = {}
for task in tasktotal:
    key, value = task.split("/") 
    # either use plain dict and test key yourself
    if key in data:
        data[key].append(value)
    else:
        data[key] = [value]
    # or use setdefault 
    # d.setdefault(key,[]).append(value)
    # or  
    # d[key].append(...) with defaultdict(list)
print(data)
Then query randomly:
import random
# random key/value-list pair
key,values = random.choice(list(data.items()))
# random item from value-list
print(key, "->",  random.choice(values)) 
Output:
'edbay': ['Submit Scan', 'Submit Example'], 
'Cafeteria': ['Connect Wire', 'Empty Garbage'], 
'Electrical': ['Connect Wire'], 'Security': ['Connect Wire'], 
'Navigation': ['Navigate'], 'Upper Engine': ['Fuel'], 
'Lower Engine': ['Fuel'], 'Shield': ['Prime Shield'], 
'Storage': ['Empty Garbage', 'Connect Wire'], 
'Admin': ['Swipe Card', 'Connect Wire'], 'Weapon': ['Clear Asteroid']}
Lower Engine -> Fuel
You could have combined answers to these 2 questions to selfanswer yours: