I hope you don’t take this the wrong way, but I’m actually hesitant to respond to everything you’ve laid out here. I don’t want to reinforce your mental consternation, especially as you’ve admitted to OCD tendencies. This is precisely the type of thoughts and questions I feel are what is keeping you in your own way. The things you are stuck on are precisely what you need to let go of. Honestly, I think you shouldn’t even weigh yourself.
To your last question, in my early days of training i very much took an intuitive approach. I logged my workouts, tried to track progress and adopted a paleo diet. I think paleo is needlessly restrictive, but it served as a great starter model for me to be more conscientious about eating without having to worry about tracking macros. So it served it’s purpose. I followed a year long program called Built for Show by Nate Green. Then i moved onto Power Training by Coach Dos which was more a template that give me a little freedom to pick my own exercises and whatnot.