Shred It! had a Title Update released at the beginning of December in 2016.
It added achievements to the Checkpoint Challenge mode, namely an achievement for completing the Checkpoint Challenge with each of the available boarders. It seems like it could be quite awkward, and can provide a some challenge if you had to play through the Checkpoint Challenge as it suggests.
However, they are actually far far easier than they are supposed to be. I'd suggest finishing the base game first, purely because you'll have likely unlocked all the characters by then already. Now, at the Main Menu, instead of choosing the Checkpoint Challenge, all you need to do is choose Chill Mode instead. Choose the character that you want to start with. and now play run through Chill Mode.
You don't have to collect the acorns or leaves, you can even fail and go into something if you want, it really doesn't matter,all you need to do is play through the five stages as normal and try to dodge some of the obstacles. The final stage is the second ice area with the moon in the sky at the back. When you make it to this stage, stop moving the controller, then after a minute or two of constant crashes, the run will come to an end on its own. A retry menu will pop up and the achievement for the character you chose will pop. Simply repeat this method for all of the characters and you will pop all the Checkpoint Challenge achievements in no time at all.
Note: You can't just idle the whole run, as the run will end on its own after too many crashes, and if you don't reach the final zone before this happens, then the achievement will not pop.
Play as Cosmo to unlock;
Play as Erik to unlock;
Play as Frappe to unlock;
Play as Jessie to unlock;
Play as Parker to unlock;
Play as Pengz to unlock;
Play as Rufus to unlock;
And finally, for completing the Checkpoint Challenge with each boarder, you'll pop;
And that's all you need to do!
Congratulations on your completion.
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