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The IRS expects estimated payments four times a year — typically mid-April, mid-June, mid-September, and mid-January — for income that isn't subject to withholding. Underpaying can trigger a penalty even if you pay in full come April, so setting aside a consistent percentage of every payment you receive is the safest habit to build.

At minimum, gather W-2s and 1099s, last year's return, mortgage and student loan interest statements, and receipts for any deductions you plan to itemize. Self-employed filers should also have a profit-and-loss summary and records of estimated payments already made.

Short-term and long-term installment agreements, 'currently not collectible' status, and first-time penalty abatement can all reduce the immediate pressure. The most important step is filing on time even if you can't pay in full — the failure-to-file penalty is steeper than the failure-to-pay penalty.

Itemizing only pays off once your deductible expenses — mortgage interest, state and local taxes, charitable gifts, and large medical costs — exceed the standard deduction for your filing status. Most filers take the standard deduction; it's worth comparing both each year, since one big expense (a new mortgage, a major donation) can tip the math.