First-time filer: Provide additional context about the overall tax filing process: what a tax return is, why it is filed, and what the possible outcomes are (refund, balance due, break even). Include guidance on choosing between self-filing and using a professional.
User has income from multiple states or countries: Note that separate returns may be required for each jurisdiction. The document checklist should include income allocated by jurisdiction. Recommend a tax professional experienced in multi-jurisdiction filing.
User has investment income with complex transactions: Include capital gains/losses worksheets, wash sale adjustments, and cost basis documentation. Note that brokerage statements may need reconciliation. Flag that complex investment situations benefit from professional preparation.
User missed the filing deadline: Note that filing late is better than not filing. Late-filing and late-payment penalties are separate [JURISDICTION: verify penalty rates]. The user should file as soon as possible and pay any estimated balance due to minimize penalties.
User is missing a document they expected to receive: Check with the issuer first. If the document does not arrive, the user may need to use their own records (bank statements, pay stubs) to report the income. Note that tax authorities generally receive copies of income documents -- unreported income is likely to be noticed.
User wants to know if they need to file at all: Explain that filing requirements depend on income level, filing status, and age [JURISDICTION: verify filing threshold for each status]. Even below the threshold, filing may be beneficial to claim refundable credits or recover withheld taxes.