Nestwise

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Why this information matters

A clean tax fact packet covering holdings, account type, realized activity, and tax context before any guidance is generated.

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Helpful notes before you fill this out

Keep user-provided tax facts separate from evidence citations.

Flag unresolved or unknown tax inputs explicitly rather than assuming defaults.

Use collected facts to drive follow-up questions before any advice logic is applied.

Examples of what to enter

Collect only the facts needed to ground the next tax question.

Prefer exact holdings, dates, and account types over vague summaries.

Use this intake to reduce ambiguity before tax reasoning starts.

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Add the real facts you know now, save progress, and come back later if something still needs to be gathered.

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Holdings and lots

These facts determine whether capital gains, losses, and wash-sale logic can be reasoned about safely.

Actual holdings, lots, and holding periods

Without lot dates and purchase history, holding-period and gain/loss treatment cannot be grounded.

Which securities or assets are involved?

What were the purchase dates, quantities, and cost basis for each lot?

Which lots are being considered for sale or harvesting?

Account context

Tax treatment changes materially based on account structure and retirement status.

Account types and retirement distribution context

Tax rules differ across taxable, IRA, Roth, and employer-plan contexts.

Are the assets in a taxable, IRA, Roth, or employer-sponsored account?

Is a retirement distribution being considered or already taken?

Are there age, beneficiary, or RMD-related constraints involved?

Realized activity

These facts anchor real tax exposure instead of hypothetical exposure.

Realized gains/losses, wash sale exposure, and tax bracket facts

Tax harvesting and timing questions depend on the actual realized picture and rate context.

What gains or losses have already been realized this year?

Were there any substantially identical purchases near recent or planned sales?

What filing status and approximate marginal tax bracket should the prep packet assume?

Retirement cash flow

Withdrawal planning is only credible when spending needs and stable income sources are explicit.

Retirement spending target and essential monthly needs

A retirement plan needs to know the spending target before it can estimate how much must come from the portfolio.

What annual spending level is the household trying to support?

How much of that spending is essential versus discretionary?

Are there any known one-time cash needs over the next 12 to 24 months?

Guaranteed income sources and when they begin

Pensions, Social Security, annuities, and other reliable income sources reduce the amount the portfolio must fund.

Which income sources are already active or expected soon, such as Social Security, pensions, annuities, rent, or required distributions?

How much does each source provide in annual or monthly dollars?

When does each source begin, and are there claiming or timing decisions still open?

Primary Social Security estimate, birth year, and tentative claiming age

A Social Security decision depends on the claimant's birth year, estimated benefit, and whether claiming may begin before, at, or after full retirement age.

What is the primary claimant's birth year?

What monthly Social Security benefit estimate is currently expected at full retirement age or another quoted age?

Is the current plan to claim early at 62, around full retirement age, or delay toward age 70?

Spouse or partner Social Security estimate, spousal options, and survivor considerations

Spousal and survivor considerations can materially change the best claiming order and the income the household can rely on later in retirement.

Is there a spouse or partner with a separate Social Security work record or possible spousal benefit?

What is the spouse or partner birth year and estimated monthly benefit, if known?

Are survivor income protection or widow/widower planning concerns part of the claiming decision?

Withdrawal and legacy strategy

Tax-smart retirement planning depends on explicit sequencing, healthcare assumptions, and legacy constraints.

Withdrawal order, Roth conversion priorities, and bracket management goals

Withdrawal order and Roth conversion priorities shape lifetime tax drag and portfolio durability.

Should withdrawals favor taxable assets, traditional retirement accounts, or Roth balances first?

Are Roth conversions being considered in low-income years or before RMD pressure rises?

What tax bracket or annual tax budget should the plan try to stay within?

Healthcare, Medicare, and long-term-care costs that could pressure the plan

Healthcare and long-term-care costs can materially change safe withdrawal decisions and cash needs.

Are there expected Medicare premiums, health events, or long-term-care concerns the plan should reflect?

Should extra liquid reserves be preserved for healthcare uncertainty?

Are HSA balances or insurance policies available to help cover those costs?

Beneficiaries, estate documents, gifting goals, and legacy constraints

Legacy goals, beneficiaries, and gifting plans affect withdrawal flexibility and account sequencing.

Are there beneficiaries, trusts, charitable goals, or gifting plans the withdrawal plan should protect?

Which accounts or assets are intended to be preserved for heirs or special uses?

Are estate documents current, and are there any legacy constraints the planner should treat as non-negotiable?

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Actual holdings, lots, and holding periods.

Account types and retirement distribution context.

Realized gains/losses, wash sale exposure, and tax bracket facts.

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