Zak: The probability that a trans* man on T will eventually experience hair loss is the same as a cisgender man. Whether or not you specifically will experience hair loss depends on genetics (for further explanation, see our article on hair loss). If you’re asking about the likelihood of testosterone causing your hair to immediately fall out, I would say the likelihood is slim but it is possible. I have heard of young trans* guys having difficulty with their hair thinning or falling out early on after starting testosterone, but again, there are cis guys the same age who struggle with the same thing (I know a few of them!).
Adrian here: This is a very complicated issue, actually. And looking to your relatives is not as useful for xx chromosomal individuals as it is for xy chromosomal individuals. Hairloss is actually not all that well understood. Please read the article that we wrote that addresses this issue more in-depth.