I'm not going to pretend John was/had much of a chance of passing pre-surgery. He basically went from being an ogre to being some sort of ghoul. The big issue with John is the same one that plagues most everything else in his life. He's lazy. John has the mentality that he can basically throw Frank's money at whatever he wants and get instant gratification. Ogre-John was able to afford the surgery, but then never bothered to learn about fashion or experiment with different styles. The most he did was buy a single black dress, then take a few pictures on a motorcycle and that was it. IIRC, he would even try and pull the "I'm not like other girls" attitude by implying he was too busy with running for office/being space commander/developing games/street racing/backchanneling/saving Israel from moon rocks to worry about such things.
This is pure speculation, but once John started trashtalking other troons, I think he had a moment of self-awareness that he didn't pass at all. So like everything else in life, John badgered Frank for money to throw at the problem and assumed it would fix everything without him having to put in any actual work, and he started harvesting his body to go from Ogre-John to Ghoul-John. Again, Ogre-John had an uphill battle, and while he wasn't passing, I think you could at least look at him and only feel a mild level of discomfort. Ghoul-John really is unsettling, to the point if I I didn't know who he was and saw him in passing, I'd probably feel a little sense of pity because I'd assume he was one of those people who was in some kind of tragic car crash or fell from a building or something and just only managed to survive and get put back together