Question: For the second Pumpkin Landing Task I need to carry five pumpkins to a shed, however I'm having quite a bit of trouble. The biggest issue I have is when I try ot proceed left, since the pumpkins have a tendency to lean the side.

What are some things to keep in mind for completing this task, and are there any tricks to make it easier?

Answer: 
When you stop walking, the pumpkins move on the opposite side you were walking just before stopping (even if it was just an instant). Forward speed has no effect.

The trick is to go towards the shed and stop a moment before the pumpkins fall.
Then just tap the direction in which they are falling and watch them going back to the center. Restart walking to the shed.
I did it! I managed to complete this right after I asked the question. It would appear that the advice the woman gives you at the start is incorrect: Your speed doesn't seem to have any affect on the movement of the pumpkins, it seems to be based entirely on time. Whether I was standing still or moving ahead at full speed the pumpkins will move at the same rate. I should point out I did not try sprinting. 

Therefore the trick is to just move as fast (without sprinting) as you can, and making sure to stop to adjust the pumpkins when they start to lean too far to the left or right.