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Pillar 2 of 3 — the core library

Explore your options

Eight 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.

Every option is tagged as an Essential core item or an Additional advanced option. Work the essentials first — see the ranked list on Essentials.

Trusts1 essential · 14 additional
Revocable, irrevocable, testamentary, special-needs, charitable. What each one does, what it costs in complexity, and when it fits.
  • EssentialRevocable living trust
  • Attorney-required
    Irrevocable trust (general)
  • Possible but risky
    Testamentary trust
  • Attorney-required
    Irrevocable Life Insurance Trust (ILIT)
Business entities2 additional
Sole proprietorship, LLC (single- and multi-member), S-corp election, C-corp, partnerships. Liability, tax treatment, compliance burden.
  • Attorney-required
    Family Limited Partnership (FLP)
  • Possible but risky
    Buy-sell agreement
End-of-life documents5 essential
Wills, living wills / advance directives, durable powers of attorney, healthcare proxies, HIPAA authorizations.
  • EssentialLast will and testament
  • EssentialDurable financial power of attorney
  • EssentialAdvance medical directive (living will + healthcare POA)
  • EssentialHIPAA authorization
Beneficiary & titling1 essential · 1 additional
How accounts transfer at death (TOD/POD, beneficiary designations, joint tenancy) and how those interact with (or override) your will.
  • EssentialBeneficiary-designation audit
  • DIY-doable
    Tenancy by the Entirety (TBE)
Insurance & retirement1 essential · 5 additional
Term vs. permanent life, long-term care, umbrella, disability. Traditional vs. Roth, rollovers, RMDs, inherited IRAs.
  • EssentialPersonal umbrella insurance
  • DIY-doable
    Qualified Charitable Distribution (QCD) from an IRA
  • DIY-doable
    Section 529 college savings plan (with Virginia state-tax deduction)
  • DIY-doable
    ABLE account (Achieving a Better Life Experience — § 529A)
Tax strategies4 additional
Lifetime gifting, annual exclusion, step-up in basis, 529 plans, QCDs, SALT workarounds, state-level estate/inheritance taxes.
  • DIY-doable
    Donor-Advised Fund (DAF)
  • Attorney-required
    Private Foundation (PF)
  • Possible but risky
    Qualified Small Business Stock (QSBS) — IRC § 1202
  • Attorney-required
    IRC § 6166 estate-tax deferral (closely-held businesses)
Healthcare & aging5 additional
Medicaid planning, long-term care insurance, Veterans Aid & Attendance, Continuing Care Retirement Community contracts, guardianship alternatives, aging-in-place strategy, elder-law foundation.
  • DIY-doable
    Medicaid 5-year lookback and transfer penalty (foundational explainer)
  • Attorney-required
    Medicaid Asset Protection Trust (MAPT)
  • Possible but risky
    Long-term care insurance (traditional + hybrid LTC-life + hybrid LTC-annuity)
  • Possible but risky
    VA Aid & Attendance Pension (wartime veterans + surviving spouses)
Cash flow & wealth-building7 essential · 1 additional
The systems wealthy families use to turn a paycheck into a plan: emergency fund, tax-advantaged account sequence, 401(k) match, HSA, Roth IRA, automated budgeting (50/30/20, Pay Yourself First, Profit First Personal). Start here before any estate-planning vehicle.
  • Essential401(k) up to the employer match + auto-escalation
  • EssentialEmergency fund in a high-yield savings account
  • EssentialPay Yourself First — automate savings before spending
  • Essential50/30/20 Rule