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In our case (not yet retired), the biggest gotchas are insurance, all different types:

Health - $2000+ out of paycheck (pre-tax, luckily my company pays 85% and we only pay 15% of the total bill) plus various copays, etc.
Life - $800+, and needs to be raised (since we have 2 more kids now).
Automobile - $2500+, for 2 1994 vehicles (no tickets, no claims, just live in South Florida and have to cover the 40%+ who carry no insurance at all).
Homeowners - $2800+, just went up over 50% this year.

That's a lot of insurance to be paying each year ! (maybe I even missed some others)
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