Short-Term Rental Tax Strategy
Specialized tax strategy for high-income earners with short-term rentals
Entity structuring. Cost segregation coordination. Material participation. Bonus depreciation. Multi-state compliance.
One CPA firm built entirely around getting this right.
How It Works
A structured path, not a menu
Most clients progress through these stages. You can enter at any point based on where you are.
Strategy Call
30-minute conversation to understand your situation, confirm fit, and outline the right starting point.
Assessment
A focused diagnostic of your tax position, identifying opportunities, gaps, and whether a deeper engagement makes sense. Fee applies as a credit toward the Blueprint if you continue.
Blueprint
Comprehensive, multi-year strategy covering entity structure, cost segregation, depreciation, and a sequenced implementation roadmap.
Advisory
Year-round strategic oversight: quarterly reviews, material participation monitoring, and proactive tax law updates.
Tax Preparation
Specialist-prepared returns with proper cost segregation integration, depreciation schedules, and entity compliance.
Bookkeeping
Monthly transaction categorization, reconciliation, and financial reporting designed specifically for STR properties.
Most clients follow this path. Enter at the stage that fits your situation.
Your Situation
Where are you in your STR journey?
Select the option that best describes you.
Exploring or Pre-Purchase
I'm evaluating whether the STR tax strategy fits my income and situation.
Learn moreI Own an STR
I have a property but I'm not sure my tax strategy is optimized.
Learn moreI Need a Full Strategy
I'm ready for a comprehensive, implementation-ready tax plan.
Learn moreI Need My Taxes Prepared
I need specialist preparation for my STR return this year.
Learn moreInsights
How we think about STR tax strategy
Where STR tax strategies go right, and where they don't.
Cost Segregation for STR Investors: When a $5,000 Study Saves $50,000 in Taxes
Cost segregation studies reclassify building components into shorter-lived assets, accelerating depreciation for immediate tax benefits. For STR investors practicing material participation, the ROI can be 10:1 or better — but only when done correctly.
Read article100% Bonus Depreciation Is Back: What the OBBBA Means for STR Investors
The One Big Beautiful Bill Act permanently reinstated 100% bonus depreciation for property acquired after January 19, 2025. This is the most significant STR tax development since the TCJA — and most investors haven't heard about it.
Read articleWhat Makes the STR Tax Strategy Work, and What Makes It Fail
The short-term rental tax strategy is frequently discussed, frequently misunderstood, and frequently executed incorrectly. The core mechanics are well-established. The execution requirements are not.
Read articleReady to find out where you stand?
See if Wakefield Tax is right for your situation.
Get StartedThomas E. Wakefield, Licensed CPA