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Coverage guides for your situation.
Start with the page that matches where you are. Each one explains the options in plain English, says who each plan type is not right for, and cites the government source for every rule.
Last updated October 18, 2026
Reviewed October 18, 2026 · 10 min
Conservative health insurance: coverage that fits your values
Four ways to get health coverage that fits your values: Marketplace, private plans, faith-based health sharing and a high-deductible core with gap coverage, side by side.
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Reviewed September 14, 2026 · 13 min
Health insurance for early retirees
Leaving employer coverage before 65? How long COBRA lasts, the options ranked by how they handle a serious diagnosis, what AARP does and does not sell, and the Medicare handoff with Medicare.gov sources.
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Reviewed October 12, 2026 · 9 min
Health insurance for real estate agents and realtors
Most real estate agents are self-employed for tax purposes, so no brokerage pays half the premium. The ways agents get covered, how commission income sets a Marketplace tax credit, the NAR health exchange, HSA-eligible plans, and the self-employed health insurance deduction. IRS, HealthCare.gov and NAR sources.
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Reviewed September 14, 2026 · 12 min
Health insurance for self-employed people: options, cost factors, and the deduction
The four ways self-employed people get covered, where a catastrophic-first plan fits and where it does not, what drives the cost, and how the self-employed health insurance deduction works. Educational, with IRS and HealthCare.gov sources.
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Reviewed September 14, 2026 · 12 min
Health insurance for small business owners
Owner-only or owner plus employees? Group plans, ICHRA, QSEHRA and individual coverage compared in plain English, with the tax treatment by entity type and IRS and HealthCare.gov sources.
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Reviewed October 12, 2026 · 10 min
Health insurance when you're unemployed: your options for 2027
Out of work and need health coverage? The 60-day window after job-based coverage ends, COBRA versus a Marketplace plan, how unemployment pay and the rest of the year's income set your tax credit, Medicaid and the coverage gap, the 2027 Medicaid work rule, and what to avoid. Every rule linked to its official source.
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Reviewed September 14, 2026 · 13 min
Losing employer health coverage: your timeline and your options
Two clocks start the day job-based coverage ends. COBRA, Marketplace special enrollment, private plans, short-term medical, fixed indemnity, and health shares compared with every limitation stated and .gov sources linked.
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Reviewed October 18, 2026 · 9 min
Missed Open Enrollment? Special Enrollment Periods explained
Losing coverage, moving, getting married or having a baby can open a 60-day Special Enrollment Period. The life events that qualify, what you may have to send, when coverage starts, and your options if you do not qualify.
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Reviewed October 16, 2026 · 24 min
What is catastrophic health coverage, and who should buy it?
Catastrophic health coverage means two things: the ACA catastrophic plan on HealthCare.gov, which only people under 30 or with a hardship exemption can buy, and catastrophic-first coverage, which any adult can build from a high-deductible core plus gap coverage. It fits healthy households that can pay for routine care in cash and want the six-figure bill covered. Educational, every rule linked to its source.
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Educational only. Not medical, legal, tax, or personalized insurance advice. Plan availability varies by state.
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