"Colossally fucking up my liver" is probably enough reason not to do something, no? Why are you taking this combo, if you don't mind me asking?
Acetaminophen in Tylenol can be very damaging to the liver and can cause liver failure and death in overdose. The max recommended daily amount is 3-4g in 24 hrs or 1-2g in one dose (guidelines vary) - any more and you are risking serious harm. What else does Tylenol PM contain? A sedating antihistamine? Drinking alcohol while ingesting acetaminophen can increase the chances of doing some damage as well, it's not a good idea.
Ibuprofen isn't heavy on the liver like acetaminophen but it can cause internal bleeding from your gut after overdose or repeated use, so again it is best to stick to the recommended dose, don't take it daily if you can help it, and be alert for abdominal pain / indigestion / bleeding. Alcohol can also increase this risk as it can irritate the stomach and promote bleeding.
Diphenhydramine and doxylamine are 1st generation antihistamines. They are sedating, and combining them with alcohol may make you pass out or could be pretty unpleasant. In high dose they cause delirium which can be truly horrendous and is not at all recreational for the vast majority of people. I would not take two different 1st gen antihistamines and I wouldn't exceed the recommended dose.
Nyquil also contains doxylamine, right? And DXM? You really want to choose one out of diphenhydramine, doxylamine, Nyquil (containing doxylamine) and Tylenol PM (if that also contains a sedating antihistamine).