Okay, I just made this copy from the site, this is the thing I would be concerned about and needs further info for you. This is the penalty thing I am worried about.
My birthday is on the first of the month.
Avoid the penalty
If you miss your 7-month Initial Enrollment Period, you may have to wait to sign up and pay a monthly late enrollment penalty for as long as you have Part B coverage. The penalty goes up the longer you wait. You may also have to pay a penalty if you have to pay a Part A premium, also called “Premium-Part A.”
When your coverage starts
The date your coverage starts depends on which month you sign up during your Initial Enrollment Period. Coverage always starts on the first of the month.
If you qualify for Premium-free Part A: Your Part A coverage starts the month you turn 65. (If your birthday is on the first of the month, coverage starts the month before you turn 65.)
Part B (and Premium-Part A): Coverage starts based on the month you sign up:
If you sign up:
Coverage starts:
Before the month you turn 65
The month you turn 65
The month you turn 65
The next month
1 month after you turn 65
2 months after you sign up
2 or 3 months after you turn 65
3 months after you sign up