To generate test cases for the "Young, Poor and Busy" problem, we need to create a function that generates random train schedules and fares while adhering to the constraints provided in the problem statement. Here is a test case generator in Python for this problem:

```python
import random
import string

def random_time():
    hour = random.randint(0, 23)
    minute = random.randint(0, 59)
    return f"{hour:02}:{minute:02}"

def random_city():
    length = random.randint(1, 16)
    return ''.join(random.choices(string.ascii_uppercase + string.ascii_lowercase, k=length)).capitalize()

def generate_schedule(num_connections):
    schedule = []
    cities = [random_city() for _ in range(100)]
    
    for _ in range(num_connections):
        start_city = random.choice(cities)
        arrival_city = random.choice(cities)
        
        while arrival_city == start_city:
            arrival_city = random.choice(cities)
        
        start_time = random_time()
        arrival_time = random_time()
        
        # Ensure arrival time is strictly after start time
        while arrival_time <= start_time:
            arrival_time = random_time()
        
        price = random.randint(1, 10000)
        schedule.append(f"{start_city} {start_time} {arrival_city} {arrival_time} {price}")
    
    return schedule

def tcgen():
    num_data_sets = random.randint(1, 10)  # Generate up to 10 data sets for variety
    data_sets = []
    
    for _ in range(num_data_sets):
        num_connections = random.randint(1, 2000)
        schedule = generate_schedule(num_connections)
        data_sets.append(f"{num_connections}\n" + "\n".join(schedule))
    
    return "\n".join(data_sets) + "\n0"  # End of input marker

# Example of generating a test case and printing it
print(tcgen())
```

### Explanation:
1. **random_time**: Generates a random time in HH:MM format.
2. **random_city**: Generates a random city name with up to 16 alphabetical characters.
3. **generate_schedule**: Creates a schedule of connections based on the number of connections required. Ensures that arrival time is strictly after the start time and that the start and arrival cities are different.
4. **tcgen**: Generates multiple data sets. Each data set contains a random number of connections (up to 2000). The function ends the input with a '0' to signal the end of data sets.

### Usage:
The `tcgen` function generates a complete set of test cases in the format expected by the problem. The generated test cases can be directly used to test the solution of the given problem.

Feel free to adjust the parameters (such as the number of data sets and connections) to generate a more diverse and comprehensive set of test cases.