Juss, great idea coming here and awesome work so far.
Here's my take since you got a lot of great info. The HRT thing is a tricky call because on one hand, a hormonal imbalance could be holding you back, but on the other, getting to a healthy weight could fix the hormonal imbalance. So I'll let you work those things out on your own.
Anyway, back to my thoughts. Living a healthy lifestyle is pretty damn simple. Most people just make it difficult because they are always looking for the next big shortcut to get them there faster.
DO NOT DO THIS. Here's some tips that may help.
1. As I said, keep it simple. Food, weights, cardio, and a strong mind will do wonders.
2. Setting goals is great, but try to stay off of the scale. Use the mirror and how your clothes fit as a guide. I'd weigh yourself no more than once a month. The body goes thru so many changes thru the day, from day to day, and the scale is the most discouraging thing you can keep around if it doesn't say what you want it to say. Lock that fucker in the attic and only get it down when you NEED to, not when you WANT to.
3. Make this process as fun as possible. Yes, getting healthy is serious for you right now, but the minute you start worrying about anything too much you will start to get burned out. This will take a long time. You're not gonna be in a size 32 waist by next year. But you don't want to be either, cause all that loose skin from losing too fast will have to be shoved in the front and back pockets. lol
The goal here is a total lifestyle change, not a diet to lose weight. The moment you realize that, the better off you will be.
Good luck to you. Great job and keep us posted.