There are no guarantees on reincarnation, at all. You could wind up being a cis male again. You could also wind up not being human. Who knows?
But, I really want to emphasize, it is NEVER too late to start transition. I have other trans friends who have put "deadlines" on their transition, and, without fail, there is always something that interferes, and results in it being put off. I have seen it cause nothing but make people miserable.
Can you move away from "deadlines" and focus on something more positive? The suggestion of celebrating milestones is a good one. What about setting goals for small things that are more reachable? Transition is a really big thing, and it inherently involves other people. It's not something that you alone have control over. Small things, even stuff like getting a new outfit or cosmetics, a new hair style or dye job, going outside dressed as female (if you're comfortable with that), all of those are little goals that may seem like not very much, but they are things to be celebrated, and they're much more reachable in the short term.
Big things like seeing a doctor for evaluation for HRT is a big milestone, as are some of the other suggestions. And those are great! But it sounds like right now, you could use some small goals to celebrate, to remind you that you ARE making progress, even if it doesn't feel like it. Focusing too much on the big things can make it feel like what you want is out of reach, and while I know the feeling of wanting it all right now intensely, it doesn't work that way. Even if you won the lotto or something and didn't have to worry about the financial aspect, and had the most supportive family and friends community, so that wasn't a worry either, it would still take time and it couldn't happen all at once.
So, please, consider setting yourself some small goals, and celebrating those, because they matter, too. And ditch the idea of a deadline, because that is just going to stress you out further. Transition is stressful enough on its own; you don't need a looming deadline and idea that if it doesn't start by then, you're screwed. And that's not the case. You've got time. I know the more it gets put off, the more depressing it is, and I want to offer lots and lots of hugs, but I also don't want you checking out because a self-set deadline has passed and you feel like it's too late. Cause it won't be. It really won't.
Again, *hugs offered*. <3