How can you tell the diet you've chosen isn't going to work well for you?

I am asking this question coming from the perspective that I have done umpteen diets throughout my life, and I can pretty much tell that in my body, anyway, I can see the signs that something is "already" not going to work well. Last year, I was following a calorie counting diet, 1300 calories per day. Last year I eventually lost 20 pounds between May and the beginning of December. Then I was "convinced" by my mother that I could take a break around the holidays and pick up after January started. Easier said than done, because over the holidays, I got some kind of affliction that made me intolerant to FODMAPS and I had to follow that diet for a while, which is totally not a weight loss diet (I gained the 20 pounds back and some). You are stuck with a slim selection of foods, and specific breads and starches, and if you want to eat anything you have to be an excellent cook - I don't cook and I don't want to. I ended up living on GF spaghetti and Low FODMAP sauce, made in the microwave. Counting calories I could get no lower than 1500, and that is 200 calories more than my body wants. When it seemed like the FODMAP problem had resolved, I chose WW Green Plan on Itrackbites/Healthi app to pick up the dieting (I am 5ft1, female and when I started in May again I was 199 lbs). I did well the first month. Then suddenly nothing. I have hit a slow dive to nothing. I tracked. I exercised. This is the point in my dieting where I start to sense "something" is wrong with the plan that I picked, and this is not going to get me even as far as I got last year.

I understand that the start of a diet is usually rather good and eventually things slow down. But I have a really slow metabolism due to Thyroid (which I have always been on meds for, they seem to make little difference) and going thru Menopause this year doesn't help that either. I have done a lot of diets, and I expect the weight loss to slow, but I sense when it starts to crash already and I haven't even lost 10 pounds yet (I have lost 8, but I know some of that was probably water), and now not only have I not lost in the last two weeks, this week my weight went up one pound. Still tracking meticulously, still exercising. Granted, last year wasn't a speedy loss either, technically on CICO I should have lost more than 20 pounds in the time period given (again, I track like a pro, and when I am in the diet mindset I am no cheater). But I was eating a lot of junk because when I do CICO, I tend to get the mindset that I don't want to waste my calories on veggies and fruit. Unfortunately, with the WW plans, they give free veggies and (depending on the plan) fruit (the plan I chose does have free fruit), so I have a tendency to eat a lot of fruit whenever I get hungry. But Itrackbites/Healthi can track both calories and Smart Points, and I haven't been overeating the fruit.

TLDR: For those of you out there who have switched which diet you are on after doing one that didn't seem to be working, how long did you hang on to the diet that was not-working before you tried something else? What are the signs you've seen that tell you "nahh, this isn't going to do it"? What rate of weight loss is too slow? Is less than two months on a diet before it starts to stall a sign? Is losing 20 pounds in half a year too slow? Any input is appreciated.

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