Some of the medals were hard, and since i had the time, i will try to explain as simple as possible how to obtain them all :)

THE ENDINGS ARE AT THE BOTTOM OF THE POST

BUNP - At the very end towards the undetected ending, instead of using "diamond" to beat the game, use "Snap neck".

IT'S A JOKE GUYS - At the very start, after selecting "sneak in" use the "liquidificator" And don't press skip. At the bottom of the sheet of paper (Aka the "note:" line) is a word "mispeled". Press it

01100010 - Towards the epic ending, when you get to the place where you can use the pokeball, Use it. When everything starts to fail, ant the error messages appear you have to quicly press ok three times, Aka close 3 error messages

LIKE A D6 - At the very start, after selecting "sneak in" use the "jumble hoppers" Three times.

FAILTASTIC - Simple and easy,fail 55 times (it doesn't have to be one exact fail, but the 55 fails have to be in a single game)

FAIL CHAMPION - You have to get 40 unique fails. 15 fails are in the "bust in" selection and 25 in the "sneak in" selection.
Bust in - you get 9 fails for making all the wrong choices and 6 fails for not making the choices at all (aka just waiting , and not selecting anything)
Sneak in - You get 24 fails for making all the wrong choices. You get 1 fail for not making a choice
(After using the "pick", when you get to the place where you can use the "bombshell", the WWII "gun" and the "plane", Don't use any of them. Just wait throughout the conversation of the guards.)

OBSCURE - You have to click 7 unique paintings throughout the game. Three unique paintings are in the "sneak in" selection and Three in the "Bust in" selection. One painting is in both selections, but it is enough click it in only one of them.

Bust in - All three of the unique paintings are in one room. Just after ramming the door you have one painting on the right. Afterwards when youre riding through the hallway there are two paintings on the wall. You have to quicly click them (It doesnt have to be in the same drive, you can click one, then fail, then retry and click the other one) You have to be really quick, it took me about 10 retries.
The other one, the one thats also in the "sneak in" selection is after selecting "Throw cable". You will see 2 guards talking, and the painting is on the wall behind them.

Sneak in - The first one is after using the "Pick" in "sneak in" selection. You have plenty of time to press it. It's on the left of the WWII gun.
The second one is towards the epic ending, After running through the guard, when you get to the place you can use the pokeball, The painting is on the left.
The third one is hard, you have to press it very quickly. In the place where you get to press four buttons, just before the epic ending, The painting appears 10+ seconds after pressing the "wheel-kinda" button, (aka the one thats on the left of the "satelite" button.) It's on the floor near the "Exit" door, but soon a peace of the ceiling falls on top of it. If you don't manage to get it, just wait until you get the epic ending and go "step back"

The one painting that's also in the "Bust in" selection is toward the undetected ending, just after using the "hammer", AND just after using the "plank". You will see 2 guards talking, and the painting is on the wall behind them.

SECRET medal - I won't say it, but i will give a hint that makes it much more easy to find.
It has something to do with a wall of text, that you get in one of the fails

ENDINGS :

UNDETECTED - Sneak in > Teleporter > Penny > Wire > Hammer > Plank > Diamond

EPIC - Sneak in > Pick > Plane > Go left > Super mushroom > "wheel-kinda" button, (aka the one thats on the left of the "satelite" button.)

AGGRESSIVE - Bust in > Ram > Shield > Throw cable > Rock > Bubble > Diamond.

I Hope i helped atleast somebody. If you have any questions of comments, Ask (or comment ;D)