Paths & Proofs

Big money decisions have a tipping point. Here's yours.

A small family of calculators for a few big, hard-to-reverse money choices — whether to convert to a Roth, when to start Social Security, whether a move to a lower-tax state pays for itself, Medigap or Medicare Advantage, and how much life insurance your family actually needs. Each one finds your tipping point — the breakeven, where waiting or acting starts to pay off.

The family, and where each one stands

Roth conversion

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Whether to move money from a traditional retirement account — an Individual Retirement Account (IRA) or 401(k) — into a Roth, paying the tax now so it grows tax-free. It models the things that quietly change the answer: how the move affects the tax on your Social Security, your Medicare costs, and how long each spouse is likely to live.

Social Security: couples

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When each spouse should start benefits. Models survivor and spousal benefits and shows the age past which waiting pays off — with every rule linked to its source at the Social Security Administration.

Relocation tax comparison

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How many years of state income tax savings it takes to pay back the cost of moving. Compares two states for your retirement income — Social Security, retirement-account withdrawals, pension, and capital gains. Property and sales tax shown alongside for context. All 51 jurisdictions, primary-source-verified to the dollar.

Medicare: Medigap vs Medicare Advantage

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How much care you'd need to use in a year before Medigap's flat premium beats Medicare Advantage's growing out-of-pocket costs — plus how your state's rules shape that premium over time and your rights to switch later.

Life insurance

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How much term life insurance a two-parent household needs, and for how long — counting Social Security survivor benefits, the survivor's own pay, and the mortgage shrinking over time.

Built by Nick

Helping family and friends work through big money decisions (when to claim Social Security, whether a Roth conversion made sense, how much life insurance a family needs), I kept running into the same problem: the tools worth using cost money or were built to sell you something. The free ones glossed over the details that actually change the answer.

These are my attempt at something better. Each one runs entirely in your browser — your numbers never leave your device — and shows its work, with every rule linked to its source so you can check it.

↗ github.com/gflo247 ↗ trakyodollas.com — spending, budgets, & net worth; free & privacy-first