TransLater

I was in a similar situation before I transitioned. 34, typically male presentation (hairy, slightly overweight, male fat distribution). I decided to start with things that weren't as "scary" to me as hormones- hair removal, voice training, getting in shape, growing out my hair. Pretty quickly I decided I wanted to start hormones.

The way I approached it was that I wanted to feel more feminine. I didn't really have an end point, but I figured I would walk down that path as long as it felt comfortable, and if it felt too much, i would stop. Eventually, my goal was to "blend" rather than pass (to me, the distinction was not being bothered in public, but maybe still having features that people would pick up on, but at a glance or in short interactions it wouldn't be super obvious).

I ended up having a very successful transition, and I pass better than most trans folks I met. I attribute it to a couple of things - voice training (I had an excellent instructor and I worked my ass off); learning about fashion and finding a style that accents my feminine features but that isn't overtly sexual, and hairstyle - lots of different looks can help soften or hide more masculine features.

A lot of it comes down to luck with genetics, and while I don't discount that, I also believe my hard work played a large factor, too. If passing is your goal, there are specific things you can focus on yo help with that. At the end of the day, the reason you are transitioning is a big factor in how you should approach it. I experience euphoria more than dysphoria, and the social aspect of being female was more important to me than specific parts of my body, so I focused on things that would let me experience society as a cis woman does, as much as was possible for me.

If you want to walk this path, walk it as far as you are comfortable going. The only person who determines where the finish line is, is you.