Might be unpopular, but: fear of addiction to weightloss

Well, I think at the beginning I was obsessive about logging everything I ate. I still log everything, but don't feel like a maniac for doing so. It often feels more like a game to me than an addiction. Although disappointed when the scale doesn't show a bunch of progress, I don't get all upset about it. I think since you've identified your tendency to embrace an either/or, good/bad, happy/cranky way of looking at things that you are not doomed. I think everything you listed in paragraph #2 will help you reach your goals. Then it looks like you'll just have to stay committed to maintaining a healthy weight after you get there.

I lost around 30lbs five or six years ago by counting calories, exercising etc. (I was using SP site), and I had the same issues. In the end, after months and months of gaining and losing and gaining and losing, I finally managed to keep those 30lbs off by making it more realistic and stopping to see everything as either very good or very bad.

As Blitzia pointed out, I too was extreme, I went from average unhealthy student diet and no exercise to 2h exercise every day, extremely healthy eating with none of my favorite sweets allowed and counted every calorie by a gram. I refused an apple from a friend because I didn't want to guess if it's "medium" or "large" sized and couldn't weight it. An apple! And if the scale didn't budge, I upped my exercise the next day to make it move. And I let the scale dictate my mood for the day, not caring about things like water weight after saltier meals or how my hormones etc. affect it.

This time around (took me only five years of maintenance to feel ready for more weight loss, so maybe my advice is not the best ) even when doing weight loss I am incorporating foods I love in my meals, I try to make them healthier and make better choices, but if I really crave a burger, I will get one, my favorite one comes from a pretty healthy place, no cheese, no meat (replaced by marinated portabello mushroom), but it's still a big burger with a bun that probably has 500kcal by itself. So, if I crave it, that will be my dinner, and instead of ordering it in, I walk to the place and back (roughly 7 miles). Same thing with my favorite chocolate, I have a small piece here and there. And over the weekend we celebrated with family and I baked a cake and had a piece of it, because it was a party. I did calculate calories in it and ate all 600 of them with satisfaction. I try to not put things into "this is good" and "this is a daemon I should avoid" categories, instead I try to have overall healthier diet and stick to my daily limit. I eat around 1700 calories (I could not survive on 1200, I would have to cry myself to sleep) and walk my 10k steps more or less every day and so far, so good?

I mean, think about your longterm goal - I don't want to weight every meal for the rest of my life and never have pizza with friends (or worse, have it and feel extremely guilty about it) or chocolate after a hard day at work, I don't want to always calculate how much calories I burned when hiking with my friends instead of enjoying doing it, but I also don't want to gain back the weight I lost, so I am trying to learn to do both - enjoy things and make healthier overall choices.

ANYTHING can become an unhealthy obsession. Usually this is caused by a combination of weird brain chemicals and imbalances, and personal history. Honestly, this is not an issue for a weight loss group, this is an issue for your Dr. We are a bunch of random strangers, some of who have very weird ideas about what is healthy or normal. Your Dr. can actually help you find medications that will help curb anxiety and obsessive behavior, and decide if you also should see a therapist to help you find the best tools for dealing with them.

The point about dieting is, if you do it with help from apps like MFP, you are tracking your progress. You are constantly (even if it is unconscious) setting and eventually reaching goals.
You are reaching the goal of tracking all your food in one day.
You are keeping in your calorie max on another.
You are managing to get down your fat intake over that one month.
And so on.
And then you lose weight and inches/centimeters.
Bam, another victory.

Reaching all of this goals triggers the "reward response" in your brain, which means a lot of happy hormones. And this reward response is basically the same that happens for addicts when they get their fix.

So yes, you can get addicted. Humans can get addicted to everything that offers a "rewarding" feeling. So the trick is to gamify something else in your life, give yourself other, healthy goals than losing another pound/kg.
Goals like working out, making someone smile each day,... whatever works for you.

I've gotten like this in the past. I totally understand what you're going through. Nowadays, I don't stress out too much about being super accurate with calories but it hasn't hindered me much.

I will say this, back about 10 years ago, I had an eating disorder and became extremely underweight. I was calorie counting back then as well. However, when I was in treatment, my RD gave me a different approach to eating. It was based on a certain number of protein servings, carb servings and fat servings. I can't for the life of me remember the specifics but it was pretty simple. It seemed to help me get to a healthy weight and not be extremely stressed out about it. I maintained my healthy weight like that for quite some time. I guess my point is that maybe you should seek help from a doctor and see if advice from a psychologist or RD could help with a plan to deal with that anxiety. It's always a thought!

Edit: I'm definitely not saying that you are on the road to an eating disorder. I just think that the advice of a doctor may help with the anxiety of calorie counting that you seem to get.

Id start by practicing counting calories at maintenance, In the meantime talk to your doctor about your anxiety. You can practice calorie counting in a less restrictive way and hopefully get your anxiety under control. Eventually you can lower calories just be aware of your anxiety and tendencies to overdo things. Inform your doctor of this and youll have someone to turn to if it begins getting excessive again. Practice makes perfect, Honestly. It isnt easy, But you being aware of your challenges means you can set yourself up to overcome them.