I don't think he's transgender in the first place. Other than growing his hair out, he's put absolutely 0 effort into his "transition", not even really basic stuff like shaving his beard. As you mention, he doesn't really fit any of the typical behaviors and he was identifying as a gay male not long ago. I think he's just a normal* straight (or maybe bisexual) male that figured out that if he can check off more oppression categories, people will give him more money and positive attention. We can see that he does this with non-gender related things like religion. Have you ever heard of someone that is an atheist, a catholic and a j-e-w at the same time? Lou claims to be all of the above depending on the day.
As for sexuality in general, he's not been very open about it but he has posted some consistent fetishes(?) for a very long time. Tall women with fur and huge fake tits have been consistent, and this new image is just a really bad example of it.
*normal in the sense of not transgender at all, be it AGP or otherwise