STR Tax Planning Calendar: What to Do Before and After You Buy a Short-Term Rental

The best tax outcomes for STR investors are the result of planning decisions made before, during, and after acquisition — not strategies applied in April when last year's returns are due. Here's a practical timeline of when to do what, and why the sequencing matters.

Pre-Purchase: The 30–60 Days Before Closing

• Run a preliminary cost segregation estimate. Before you close, model the expected year-one depreciation deduction based on purchase price, property type, and furnishing plan. This affects your investment analysis and financing decisions.
• Confirm your STR loophole eligibility plan. Will you be managing the property personally? How will you track participation hours? What platforms will you list on, and what average stay does your market support?
• Review entity structure with your CPA. Should you hold the property personally, in an LLC (disregarded or partnership), or in an S-Corp? The answer depends on your asset protection needs and how you plan to use losses.
• Get a property tax assessment breakdown. Request the county assessment card before closing — this determines your initial land allocation for depreciation purposes.

At Closing and Month 1

• Commission your cost segregation study. Order the study as close to acquisition as possible — ideally within the first few months. Studies are more accurate with fresh documentation and site visits close to the transaction date.
• Start your participation hours log. Begin tracking your management hours from day one. Use a calendar app or dedicated log. Document every booking management session, maintenance coordination, and property visit.
• Open a dedicated business bank account. Separate rental income from personal funds from day one. This simplifies bookkeeping and substantiates your rental activity for tax purposes.
• Document the furnishings inventory. Photograph and inventory everything included in the property (especially if it came furnished) — this documentation supports the personal property classification in your cost seg study.

Ongoing: Monthly and Quarterly

• Reconcile rental income from platform statements against bank deposits monthly
• Track and categorize all operating expenses (receipts, invoices, platform fee statements)
• Update participation hours log weekly — don't let it fall behind
• Review estimated tax payments quarterly — especially in year one with large cost segregation deductions, you may need to adjust withholding

Year-End Planning: September–December

• Confirm your material participation status. By November, you should know if you're on track to meet your participation test. If you're borderline, October and November are the time to put in additional hours.
• Assess your depreciation deductions with your CPA. Review the cost seg study results and how they interact with your income. Plan estimated tax payments accordingly.
• Consider additional capital expenditures before year-end. Furnishings and improvements placed in service before December 31 qualify for the current year's bonus depreciation. Major purchases like hot tubs, outdoor furniture packages, or appliances are worth timing to year-end.
• Review your personal use days. If you've stayed at the property for personal purposes, count those days and confirm you're below the 14-day/10% vacation home threshold.

Tax Filing Season: January–April

• Compile all 1099-Ks from Airbnb/VRBO and reconcile with platform earnings statements
• Provide your CPA with the completed cost segregation study and 481(a) calculation
• Ensure Form 3115 (if applicable for a look-back study) is prepared and filed with your return and the duplicate sent to the IRS
• Review the depreciation schedule for accuracy — every component should be on the schedule at its correct MACRS class