Pillar 2 of 3 — the core library
Explore your options
Six categories, each a neutral, well-sourced walkthrough of the relevant options. No recommendations — facts, tradeoffs, and the specific places state law changes what's available to you.
Trusts15 options
Revocable, irrevocable, testamentary, special-needs, charitable. What each one does, what it costs in complexity, and when it fits.
- Possible but riskyRevocable living trust
- Attorney-requiredIrrevocable trust (general)
- Possible but riskyTestamentary trust
- Attorney-requiredIrrevocable Life Insurance Trust (ILIT)
Business entities2 options
Sole proprietorship, LLC (single- and multi-member), S-corp election, C-corp, partnerships. Liability, tax treatment, compliance burden.
- Attorney-requiredFamily Limited Partnership (FLP)
- Possible but riskyBuy-sell agreement
End-of-life documents5 options
Wills, living wills / advance directives, durable powers of attorney, healthcare proxies, HIPAA authorizations.
- Possible but riskyLast will and testament
- Possible but riskyDurable financial power of attorney
- DIY-doableAdvance medical directive (living will + healthcare POA)
- DIY-doableHIPAA authorization
Beneficiary & titling2 options
How accounts transfer at death (TOD/POD, beneficiary designations, joint tenancy) and how those interact with (or override) your will.
- DIY-doableBeneficiary-designation audit
- DIY-doableTenancy by the Entirety (TBE)
Insurance & retirement6 options
Term vs. permanent life, long-term care, umbrella, disability. Traditional vs. Roth, rollovers, RMDs, inherited IRAs.
- DIY-doableQualified Charitable Distribution (QCD) from an IRA
- DIY-doableSection 529 college savings plan (with Virginia state-tax deduction)
- DIY-doableABLE account (Achieving a Better Life Experience — § 529A)
- DIY-doableHealth Savings Account (HSA) as stealth retirement
Tax strategies4 options
Lifetime gifting, annual exclusion, step-up in basis, 529 plans, QCDs, SALT workarounds, state-level estate/inheritance taxes.
- DIY-doableDonor-Advised Fund (DAF)
- Attorney-requiredPrivate Foundation (PF)
- Possible but riskyQualified Small Business Stock (QSBS) — IRC § 1202
- Attorney-requiredIRC § 6166 estate-tax deferral (closely-held businesses)
Healthcare & aging5 options
Medicaid planning, long-term care insurance, Veterans Aid & Attendance, Continuing Care Retirement Community contracts, guardianship alternatives, aging-in-place strategy, elder-law foundation.
- DIY-doableMedicaid 5-year lookback and transfer penalty (foundational explainer)
- Attorney-requiredMedicaid Asset Protection Trust (MAPT)
- Possible but riskyLong-term care insurance (traditional + hybrid LTC-life + hybrid LTC-annuity)
- Possible but riskyVA Aid & Attendance Pension (wartime veterans + surviving spouses)