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Taxes & Reporting

Turn a year of raids into clean records: cost basis, tax lots, 1099s, and fewer tax-season ambushes. However, if you've read my book: Get 20% Returns With Dividend Capture, you know I only use my IRA accounts for dividend capture. I highly, highly, recommend you talk to your tax expert before you use a regular trading account for Dividend Capture.

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FAQ (fast answers)

Quick answer: Taxes & Reporting tools help Yield Raiders keep records clean—cost basis, tax lots, exports, and 1099-ready reports. If you’re doing dividend capture outside an IRA, talk to a tax pro first, because frequent short-term trades can create complex reporting and surprises.

What is this category for?

Taxes & Reporting tools help Yield Raiders keep their trading paperwork sane—especially when you’re doing lots of short-term in-and-out trades. Think: downloading 1099s, verifying cost basis, choosing the right tax lots, exporting trades, and generating clean reports so you (or your tax software) can handle 1099-DIV / 1099-B activity without a nervous breakdown. But let me warn you one more time. Talk to your tax expert before you engage in dividend capture in any account outside of an IRA.

What should a Yield Raider look for?

Look for tools that (1) import from your broker reliably, (2) track cost basis and tax lots accurately, (3) export clean CSVs, (4) help with Form 8949-style reporting for trade-heavy accounts, and (5) keep an audit trail so you can explain what happened later. Bonus points if it reduces “oops, wrong lot” mistakes.

Do I need special “trader tax” tools?

Usually not—but if you generate a mountain of trades, an 8949-focused tool can save time and errors. If your situation is complex, loop in a tax pro. The goal here is clean inputs and clean reporting—not DIY heroics.

Charles Schwab Tax Center

1099s, gain/loss reporting, cost basis, and downloadable tax forms—straight from the source.

Best for: grabbing official tax docs and verifying cost basis/tax lots. Why Yield Raiders care: your broker’s numbers are the “ground truth” your tax filing usually starts from. Watch-outs: exports vary by account type; always double-check lot selection if you trade around ex-dates.
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IRS Online Account (Transcripts & Records)

View key IRS account info, transcripts, and filings—helpful when something doesn’t match.

Best for: verifying IRS records and retrieving transcripts when you need proof. Why Yield Raiders care: if a broker form goes sideways, transcripts help you reconcile what’s on file. Watch-outs: identity verification can be annoying; do it once and you’re set.
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IRS Free File

Free guided filing options (income-eligibility dependent) through IRS partners.

Best for: potentially filing for free if you qualify. Why Yield Raiders care: saves money when your return is straightforward (even with 1099s). Watch-outs: eligibility rules vary; always start from IRS.gov, not random ads.
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IRS Direct Pay

Pay IRS taxes directly from a bank account—no third-party middleman.

Best for: making payments safely and confirming they went through. Why Yield Raiders care: if you owe (short-term gains can do that), this is the cleanest “pay it” option. Watch-outs: triple-check tax year + payment type so you don’t misapply it.
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TurboTax

Big-name tax filing with imports for common broker tax forms (varies by tier).

Best for: mainstream filing workflows, broker form imports, step-by-step guidance. Why Yield Raiders care: handles 1099-DIV / 1099-B activity if you’re on the right product tier. Watch-outs: “free” can be conditional; confirm pricing before you invest hours entering data.
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H&R Block Online

Online filing with upgrade paths for investments and broker tax forms.

Best for: filing with optional human help and online workflows. Why Yield Raiders care: a practical alternative when you want guided filing plus investing support. Watch-outs: pay attention to upgrade prompts—investment handling may not be in the base tier.
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FreeTaxUSA

Low-cost online filing that supports common investment forms (good value if it fits you).

Best for: budget-friendly filing with investment support. Why Yield Raiders care: if you’re paying out the nose for filing, this can reduce friction and cost. Watch-outs: state filing typically costs extra; confirm features before committing.
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TaxSlayer

Online filing with tiers that cover investments, 1099s, and more complicated returns.

Best for: tax filing when you have investments and want a simpler UI. Why Yield Raiders care: helps process investment income without paying “big brand” prices (depending on tier). Watch-outs: compare tiers—investments may push you out of the free option.
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TaxAct

Another mainstream online filing option with investment support (tier-dependent).

Best for: filing with investments when you want another alternative to the “usual suspects.” Why Yield Raiders care: more choices = leverage; you can pick the one that handles your forms cleanly. Watch-outs: confirm investment support and total price before you start entering everything.
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TradeLog

Tax-focused trade reporting with Form 8949-style outputs for trade-heavy accounts.

Best for: heavy trading histories and cleaning up reporting for lots of transactions. Why Yield Raiders care: dividend capture can generate many trades—this helps keep the paper trail clean. Watch-outs: imports can take setup; test with one account/export first before going “all in.”
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Koinly (Crypto Tax)

Crypto tax reporting and transaction imports—useful if you also dabble outside stocks/ETFs.

Best for: crypto transaction tracking + tax reports. Why Yield Raiders care: some folks run “income” strategies across multiple asset types—this keeps crypto from wrecking tax time. Watch-outs: exchange imports can be messy; reconcile totals before generating final reports.
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CoinTracker (Crypto Tax)

Crypto portfolio + tax reporting with exchange/wallet connections and exportable reports.

Best for: tracking crypto activity and generating tax-ready summaries. Why Yield Raiders care: one messy asset class can contaminate the whole return—this helps quarantine the chaos. Watch-outs: check plan limits and supported exchanges before importing a big history.
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