re: Would you rather retire at 55 ok-comfortable or retire at 65 very comfortable-leave estate

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Once you hit 65 you will get SS & Medicare which should offset monthly expenses. I guess it all depends on how bad you want to retire early.

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Some people assume Medicare is free, my wife recently enrolled, her expenses for Medicare

Part A free
Part B required $130/month
Part B supplement, not required, but a simple medical issue could cost you thousands without it. $175/month
Prescription drug plan $34/month
Vision plan $14/month
Dental plan $30/month

$383/month total, when I enroll next year that will almost double, and the cost always goes up.