How about if you get sick January through September most years? Even then, you won't get coverage until the first of the next month if you've applied by the 15th, or the first of the second month following otherwise.
Clarification: If you get sick Oct - Dec you’re “in luck”, except for the month-following delay.
Personally, however, I’ve never been able to schedule my ER visits for heart failure and strokes reliably that far in advance.