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Thank you for the question and I am happy to help.
1. You have a history of irregular periods and irregular bleeding
2. You had a myomectomy in July followed by a period in early August
3. You have diabetes, thyroid disease, hypertension and high cholesterol
4. Pregnancy tests and ovulation tests are both negative
My guess is that you have a condition consistent with PCOS or polycystic ovarian syndrome. This is very common in women and it leads to a state of not ovulating. Consider the first day of your period as Day1. Most women ovulate around day14 and get their period on day28. When you do not ovulate, then you do not get your period and the lining of the uterus may very well starting shedding irregularly. Some women think that they are getting a period but it is just random bleeding. The stretches of time with no bleeding are confusing for many women and this is almost always in the setting of negative pregnancy tests.
It sounds like you are likely trying to get pregnant given that you are trying to track ovulation. You have a lot going on that is contributing to the problem with the main things probably being related to diabetes and insulin resistance. It is my guess that the myomectomy has nothing to do with all of this. In women with anovulatory cycles who are diabetic, they often need oral diabetes medications and fertility drugs to regulate their cycle.
I am sort of rambling on, but I think that this answers the original question of 'what can this mean'. Please give me some feedback and we can work through this confusion to your satisfaction.