Transfem

You are going to change slowly and gradually once you start HRT. That's the most important thing. Get that started as early as possible.

I would advise you to freeze your sperm before you start HRT, unless you are sure you don't want children. The informed consent documents listed two irreversible changes, sterility and breasts.

I'm about 3 and a half month on HRT. I barely have breast shape at this point. My measurements have not changed enough that my old clothes no longer fit comfortably. You'll have time to adjust to the changes. You'll have plenty of time to gradually upgrade your wardrobe, and learn makeup, there's no need to work these things out in advance.

Delay is fine for everything except the HRT and cryopreservation if applicable. Get that E, sis!

I will add to the other excellent comments here: there are no perfect times. Waiting for everything to align just so will prevent everything from ever happening. Pick a goal and start it. Now. It seems like you took the first step, so congratulations! I'm not bitter about it, but I am an example of what happens when you wait for perfect alignment. You may wake up one day and say "why did I let the last decade go by in a fog instead of taking action" and regret missing some of your best years living as the real you. Don't wait for any conditions, just improve the ones you have as you go.

I haven't earned that

Stop right there. You have a medical condition that needs treatment. No one earns medical care, it's a necessity.

I agree with everything the other commenter said, thrift your clothes, and start with simple makeup. It will help you familiarize with women's clothing sizes (they are nebulous), and what styles you enjoy. The more time you have practicing eyeliner, eye shadow blending, and blush placement, the better it will look when you're ready to wear it in public and the more confident you will feel. I used to just sit with YouTube makeup tutorials and practice with them until I found things I liked

I wouldn't delay on HRT, I think it should be the first thing people do.

Some advice that's helped me is this: Stop saying "should". "Should" implies that there is some objectively correct action to take in your situation, but there isn't. Ask yourself if an action aligns with the kind of person that you want to be. You can absolutely do any of these things if you believe they align with your personal values, but you don't NEED to do anything. Without that pressure of trying to perform correctly to meet some external criteria, you can decide what you want to do based on your own values.

Anyway, I might not be describing the concept clearly, but I hope it's something that can help you.

I bought femme clothes from thrift stores. It's cheap, I could swap out equivalent masc clothes that I didn't anticipate needing. It got easier over time as a sense of style developed. I'm 3.5 months HRT and 90% of my clothing was purchased pre-HRT, no significant size changes yet. Exception: Bras were mainly purchased after.

For makeup, even in boy mode a little foundation and blush made me feel cuter. The key with makeup is subtlety. And a lot of foundation to hide shadow, if that's a concern.

Finally, a skin care routine did wonders for me, especially once HRT began. I use CeraVe cleanser, moisturizer, and a Neutrogena retinol cream between them every other day at night, plus a Neutrogena sunscreen in the morning. It had super noticeable softening effects on my face within two weeks.

What helps me is: you can experiment with all this stuff without necessarily taking it out of your bedroom if you don't want to. You can wash off the makeup. Or you might feel great and go out.

Good luck!