Track lodging and occupancy tax obligations, plus nexus issues across platforms. Separate personal use carefully. Understand depreciation schedules, potential bonus treatment, and how improvements versus repairs affect timing. Long‑term rentals may qualify differently from nightly stays. Consult a knowledgeable professional before year one ends. Smart structuring converts messy paperwork into durable advantages, leaving more of your hard‑earned yield exactly where it belongs.
Underwriters reward predictability. Many prefer documented long‑term leases, while some specialized lenders support hospitality‑style income with stricter underwriting and reserves. Keep clean books, show trailing actuals, and present conservative projections. Interest‑only periods, rate caps, or amortization choices reshape cash flow profiles. Align your capital stack with your operational reality, ensuring the financing story harmonizes with the income engine you actually run.
Decide whether you will sell based on stabilized NOI, refinance after improvements, or pivot between leasing models. Appraisers weigh comps, income stability, and documented operations. Short stays may command premiums in proven corridors or discounts where regulation feels fragile. Package records beautifully, including maintenance logs and reviews. Strong documentation is marketing for buyers and banks, unlocking outcomes that spreadsheets alone rarely achieve.