Diabetic turning 26 next month/leaving job: need help navigating insurance options

Hi,

I’ve posted on here before but I am looking for more clarification. I turn 26 late next month so I’ll be getting kicked off my mom’s health insurance. I currently have a job that offers insurance, but I am planning to leave the job ASAP… however, I may not hear back from the job I really want until early January, and don’t want to haphazardly accept a job that has red flags (that’s what got me into my current situation). Plus, any job I’ve applied for has a 1-2 month lapse in coverage.

Anyway, I’m a Diabetic and my insurance is denying my LAST fucking 3 month supply of insulin. Trying to fight for it. My mom does not want to COBRA me because it’ll be $800. My current job’s insurance would be $285… but not sure how much it’d be if it were COBRA’d. The best health insurance plan I could find on the Marketplace for cheap was one for $600.

Questions:

Is it best to switch to the Marketplace one, or leave my job and COBRA theirs? Marketplace sounds less complicated because won’t have to go through the COBRA process, and the potential complication in my 2nd question.

If I signed up for my job’s insurance in early January and it didn’t take effect for a month and by that point I’m gone or leaving, can I still COBRA it?