Your last week as vacation idea is not proper.
This should be your plan:
O being last day at old job, N bing first day of new job.
O - 14 to O: You give notice, get paid salary, have medical insurance.
O + 1 to end of Month: You still have (free) medical insurance by the end of that month (if you quit on 7/1, whole July is free medical insurance). Starting the following month, if you don't have medical insurance from new company, you'll have to buy medical insurance under COBRA, which allows you to buy insurance under the price from your old employer for 18 months.
O to N: you have some vacation pay from your old job. Otherwise you are not getting paid.
N and N+.... You get paid at the new job. I hope the new health insurance starts. but sometimes the medical insurance doesn't start, so you have to pay for old insurance under COBRA like I said before.
This should be your plan:
O being last day at old job, N bing first day of new job.
O - 14 to O: You give notice, get paid salary, have medical insurance.
O + 1 to end of Month: You still have (free) medical insurance by the end of that month (if you quit on 7/1, whole July is free medical insurance). Starting the following month, if you don't have medical insurance from new company, you'll have to buy medical insurance under COBRA, which allows you to buy insurance under the price from your old employer for 18 months.
O to N: you have some vacation pay from your old job. Otherwise you are not getting paid.
N and N+.... You get paid at the new job. I hope the new health insurance starts. but sometimes the medical insurance doesn't start, so you have to pay for old insurance under COBRA like I said before.
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