An important note, you don't have to restart the level if you fail. Just keep trying and you'll get the achievement once you complete a successful run.
Trouble with the trolley, eh? This guide will hopefully help you out.
First you'll have to earn access to the area where the challenge takes place. There's a jump boost that requires 14 spirits to activate, which is located here -
The challenge will probably take a few tries to get the hang of. You steer the trolley across lanes with
, fire the cannon with
and jump with
. At certain points you'll have to fire at a sign to switch from one lane to another.
Also present on the course are mechanical arms which drop one of two things onto the track, which are randomised. The first is a small brown crate, which you have to jump over. The second is a TNT barrel, which you must fire at with your cannon to clear.
As long as you don't crash, the track loops endlessly so don't worry about having to restart if you miss a turnoff. Also, you'll collect gears even if it looks like you're jumping over them to avoid an obstacle, such as at 1:08 in my video.TheDonSimeoni
Recommends using the d-pad to move the trolley rather than the stick for more accuracy.
I've included a video below showing an optimal route. One of the more annoying challenges in the game but you'll do it, promise