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I agreed to help the Mafia (your request of payment doesn't matter) and went back to John Smith and told him about the not-so friendly friends he has waiting outside for him. Naturally I failed the mafia's quest of luring him outside to get shot, but now I have to help John escape. After getting the dress and wig, I still had 8 hours and 30 minutes left to do things, but I decided to go home. (I don't know if the time you have left will affect his death, but I think agreeing to the mafia's quest of luring John outside might have triggered them to wait until you "complete" the quest and in doing so, not kill John the second he walks outside normally at the end of the day.) I went to the merchant and bought a fake pass from him. The next day, I gave John the items and now he can be a pretty lady walking home and resign from the ministry.
This is how I did it.
I didn't work on this day, I just did the quest and nothing else.
Tell John [Tony] about the fire and his family, he takes the ring off you and you get the reward for helping him.
After the conversation with him go back outside, you will get approached by a "Stranger" who wants your "assistance".
Refuse to help him, he'll say that they have a long reach anyway.
if you want to help John [Tony] and you have refused the "stranger" go back to John [Tony] and tell him about what happened outside and that you will help him.
He'll tell you he needs a disguise to get past them.
Talk to Page, the courier by DeSalvo's office, and get the wig from him you'll need to buy it from him for $300 if I recall.
The dress is in Gloria's cubicle, you'll need to search it to get it, but it's better to not touch it at all for now, or you'll get stopped by security.
You need to use your apartment door for this next part
Why you can't get it from the courier, by doing a deal there is daft as he sells you a wig anyway(!) but that's not the point here.
Go home.
Go to the Merchant and buy the fake pass from him. Can't recall how much [$150-300].
Next Day go to work, then get the dress from Gloria's cubicle.
If you do this the day before you have the pass, and you if you took the dress, then you get a stop and search by security. Options available here as to how to react to the guards, pay them or use Authority etc.
Go to work [12th floor]
If you don't already have the dress, then search Gloria's Desk for it
Then talk to Tony and give him the wig, dress, and the pass.
He then walks out of the building and gets a wolf whistle as he walks past some men.
Job done.
Hopefully I've remembered it all, correctly.
Edit: Forgot to say this about John Smiths desk
Get items from it before you give him the disguise, because his terminal will be taken over by a new person and you will not have access to it after you've helped him.