Weight loss as a dietary goal is a recipe for disaster, particularly if you're expressing significant health conditions already, which you've indicated you do.
Suck it up and stop letting your mind wind you around in circles, your body knows much more than your brain and is holding onto that weight for very good reasons.
You say you're well read and intelligent, hence you should then have a clear idea in your head of what a healthy diet consists of and you are talking about making unhealthy changes for the sake of weightloss, knowing full well it will cause further damage to your body, that's the sort of logic your brain is giving you?
Settle on a healthy diet and start to deal with the real issues you have expressed, the sleep issue is a major one and you need to do some real research in regards to circadian rhythms, modern life with late night TV, computers and I phones in bed can have very negative effects on circadian rhythms, this is likely where a vast number of your issues lie.
In addition to that, as suggested, get some serious testing done to determine whether there are any other underlying deficiencies you have, both minerals and vitamins, and if so do appropriate research to guide yo as to how to balance these, many have opposing interactions and you usually have to take multiples to geta a balanced process.
You are not morbidly obese, and with all the exercise and movement are likely physically fit, from a skeletal muscle point of view, so that probably puts you far ahead of the majority of the population, the weight issue is most likely driven by psychological perceptions, and I understand at your age it is a bit tough in that regard, but you still need to make long term choices, and chasing a short term target may have serious long term side effects.