Thank you, I hope I pushed the right buttons. Shit happens too us all and sometimes we fall into stupid traps emotionally and they affect much in many ways.
Your best strategy is to come up with a stable base diet that can be easily modified for a hardcore cut or a lean bulk. This is basically the old animal protein, healthy fats, veggies, and clean carbs added after lifting. Then breakfast is the next step, then possibly a little at other meals.
You would do better to get lean as possible, then slowly work back up. Since summer is coming anyway, the leaning out (not so much cutting full blown) is a good strategy.
You wrote spills, but I want you to read the articles, the spills are good, but use those to interact. Certainly come back here to fine tune if you want.
As for the insecurities bit, this is something CT mentioned in a recent spill. I hope you take my blunt highlighting of attitude and effects as a friendly reminder not an attack. I certainly won't claim I am above such faults (though like many, often I would like to believe so and am probably lying).
For example my own situation when I started was I wanted to gain 20-30 pounds LBM and lose 10 pounds fat. Instead I got caught up in powerlifting and getting bigger. This is silly because my main sport activity is windsurfing, particularly wave sailing - down the line and jumping. I didn't stick to my personal goals and let others' ideas lead my actions.
Anyways, study the articles, and when in doubt keep it simple. In time you will surpass what you thought you could achieve. Focus your energies on the rest of life, go with the flow and enjoy the ride.