What separates a great contractor from a costly mistake when rehabbing a short-term rental?
In this video, Dave breaks down the essential questions every STR investor should ask before hiring a contractor for a renovation project—especially if you’re racing to complete a rehab in time to take advantage of cost segregation and bonus depreciation opportunities.
You’ll learn how to evaluate a contractor’s experience with investor-owned properties and short-term rentals, spot red flags in timelines and budgets, manage change orders, verify subcontractor reliability, and structure payment schedules that protect your investment. Dave also covers STR-specific design decisions that can reduce maintenance costs, improve durability, and maximize long-term returns.
Topics covered:
✅ Contractor experience and STR-specific projects
✅ Change orders, cost overruns, and budget protection
✅ Realistic timelines and project management expectations
✅ Subcontractor oversight and accountability
✅ Permits, inspections, and local market knowledge
✅ Durable design choices for high-traffic vacation rentals
✅ Cost segregation documentation requirements
✅ Draw schedules, deposits, and payment milestones
✅ Reference checks and the most important questions to ask past clients
Whether you’re planning a cosmetic refresh or a six-figure gut renovation, these questions can help you avoid delays, control costs, and hire with confidence.
What questions have you found most valuable when interviewing contractors?
