I'm pretty sure Tiffany just doesn't want to work and is happier with e-begging his "fans" for money. If he does have carpentry skills, it shouldn't matter whether he goes to work wearing lipstick or not. And he strikes me as someone who's not afraid to use the legal system to his advantage - remind you of anyone? I can totally see him pulling some shit where if he got rejected from a job, he'd come back at them with a lawsuit alleging that it was all because of his oppressed tRaNs IdEnTiTy. I get that it's hard for ex-convicts to find work, but I know plenty of people with felonies who have jobs. And especially when you're working in construction... they pretty much give no fucks as long as you're willing to show up and do the work.
Bottom line, Tiff could absolutely work if he wanted to. He's just happier smoking weed and sputtering his way through incoherent, twacked-out videos all day. He's so proud of being a "socialist," but that's just because he thinks socialism will give him free weed and hormones.
Edit: oh shit. I just saw that he posted a new video yesterday where he complains about people misgendering HIS KID. God I feel so bad for that poor little kid. I hope he's able to see through the ridiculousness and doesn't buy into the "gender identity" that his trooner dad is trying to force onto him. Tiff also says that he wants facial feminization surgery but will never get bottom surgery or alter his voice. Hmm. At the end of the video the kid is dancing in the background without a shirt or pants on, but you can't see below his waist. Luckily Tiffany, World's #1 Mom, uses this moment to tell him to go get dressed.