I'm going through a rough patch in my career and am considering retiring with my $5 million portfolio - how can I handle health insurance though?
Briefly

Health insurance and out-of-pocket costs can reach thousands a month, making healthcare planning crucial for those considering early retirement.
FIRE isn't just about reaching a financial goal; it's about ensuring your plans for retirement, including healthcare, are thoroughly thought out and manageable.
For early retirees, understanding the nuances of healthcare, especially the Affordable Care Act's silver and gold plans, is vital due to the potential high costs involved.
Those with pre-existing conditions, like cancer, must emphasize healthcare planning even more, highlighting the need for a strategic approach to early retirement.
Read at 24/7 Wall St.
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