How to Escape from Cougar Creek Railroad
-The first escape My Little Phoney is (from what I know) only achievable playing single player. You will have to sneak around the train and obtain a green pen, an orange pen, and a hankerchief. None of these items are contraband so you can be caught as many times as you like and still have them. Once you have all 3 items go to the carriage with the horse running alongside it (towards the back) and craft the fake carrot in the crafting menu. You can then walk up to the opening in the carriage and escape.
-The second escape Hooked On You is (from what I know) only achievable playing single player. You have to obtain two crowbars, a piece of ductape, and a rope. All of these items are contraband but if you are caught holding one it should reapear in the contraband desk next to the control room. Once you have all these items you must craft a grapple head and then a grapple hook. From here go to the carriage with the ladder in it (towards the front) and climb on top. You can then escape on the east side of the carriage.
-The third escape, Do The Locamotive is probably the hardest escape possible. You have to obtain weapons from anywhere in the train, make your way all the way to the front, and take out all 3 guards present in the front. It is very straightforward however it can be challenging taking out all 3 guards as they all have good weapons. This escape can only be done in multiplayer.
-The fourth escape Loose Caboose is another challenging escape. You must get 3 crowbars (I am unsure if 3 crowbars will always spawn but I played 4 games in a row and every time I got 3 crowbars so I believe the chances are very high) and detach the caboose at the end of the train. The crowbars can be obtained in any desk in the train and are contraband so they will be taken if you are caught but they should reapear in the contraband desk next to the control room. Once you have all 3 crowbars get everyone on the back of the train and detactch the caboose.