I find myself wondering why Zack didn't try to get SSI seven or eight years ago, when Social Security was handing out tugboats to tons of trannies... and I've come up with several reasons why he never tried. First, you need to have someone treating you for a sustained period of time, someone to diagnose your mental illness and attempt to treat it. They would have to be able to demonstrate that the illness or condition would interfere with your ability to work. Zack, so far as I know, has never been treated for mental illness or seen a counselor or therapist. Zack's ego would never allow him to sit there and listen to a therapist tell him uncomfortable truths about himself, nor would he consent to a treatment plan that involved anything other than "Let me do whatever I want, whenever I want, and avoid all responsibility. Oh, and give me whatever psychiatric drugs I want, to be taken if and when I see fit."
Second, there's the aspect of being unable to work. Zack has never held a job other than "making videos on youtube", which is not considered work by Social Security. You have to work for a certain period of time in real jobs making a certain (low) amount of money to qualify for SSDI. You need to have paid FICA taxes for a period of five to ten years. Zack has done none of this, so SSDI is out the window. Zack would have to try for the lower-paying SSI, which is designed for people who are so profoundly disabled that they've never been able (or probably ever able) to hold a job of any kind. it's a lower amount by design, because people that deeply unwell generally have family taking care of them (think Hartley Hooligans) or are in the care of the government in the form of group homes or long-term care facilities (think of a profoundly autistic man who has outgrown the care and control of his parents). Once again, though, Zack doesn't meet the requirements.
So why didn't Zack ever even try? First, the treatment and diagnosis issue I mentioned earlier. Second, there's Zack's gargantuan ego. He never can resist trying to show everyone he comes into contact with just how smart he is. Filing for disability is, by definition, admitting that you have serious, deep, constant problems. Zack ain't going for that. The most important reason, however, ties back in with that first point: Zack is profoundly, deeply lazy. Going to therapists takes effort. Filling out paperwork for an application takes effort. Interviews with Social Security disability evaluators takes effort. It's much easier to sit on your giant dildo, fuck around on the internet, and live off of your wife's earnings.
Well, it's too late now. Social Security has a huge backlog, and I've heard (anecdotally, admittedly) that trannies aren't regarded as special or guaranteed slam dunk cases now. You better have something wrong with you and you better be able to prove it.