This one is pretty simple, you just need to play as rosedoodle and crash out in such a way that the camera gets a shot of her upskirt. You may get this one just from playing regularly if you play a lot as rosedoodle! Below is an example, this is the shot that I got the achievement with.

This one is very simple. On the skater select screen you should notice a display in the background to the left. On the bottom shelf is one of those booby mousepads, just click on it! Below is a screenshot of the screen you should be on. The item is just above the decal of a pink bunny sleeping.

This achievement is unlocked by obtaining one of the skateboards that grants you an advantageous ability! So all you need to do is just keeping using the gacha machine until you get one basically. Below is a screenshot of a skateboard that grants you a cheat ability.