My insurance company (UHC) goes by the initial weight when you first meet with the doctor. They do not penalize you if you lose weight. Your insurance may be different. Even if you have the same insurance as another person, a lot of the criteria is determined by the contract your employer negotiated for their benefit coverage. I know another person with UHC in Missouri, different employer, we both had a 6 month diet, but she had to visit a physical therapist and I did not.
Based on your height and weight, I doubt the insurance company will disqualify you. At 5'5" you could drop to 210 and have a BMI of 35. Some insurance companies require one or two comorbidities below a BMI of 40.