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STR TAX STRATEGY
Tax strategy for short-term rental investors.
Wakefield Tax provides specialized tax advisory for investors using short-term rentals to build wealth and reduce their tax burden.
LICENSED CPA | STR SPECIALIST
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STR TAX STRATEGY
Tax strategy for short-term rental investors.
Wakefield Tax provides specialized tax advisory for investors using short-term rentals to build wealth and reduce their tax burden.
LICENSED CPA | STR SPECIALIST
Analysis
Market
Growth
Strategy
Planning
Analysis
Market
Growth
Strategy
Planning
Analysis
Market
Growth
Strategy
Planning
Analysis
Market
Growth
Strategy
Planning
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WHO WE ARE
Institutional-level expertise. Specialized focus.
Built on a foundation of top-10 firm experience, Wakefield Tax brings institutional-quality standards to a specialized practice. One focus. Direct access.
bonus depreciation now permanent
bonus depreciation now permanent
bonus depreciation now permanent
average stay threshold
average stay threshold
average stay threshold
hours to qualify
hours to qualify
hours to qualify
strategy, complete focus
strategy, complete focus
strategy, complete focus
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OUR APPROACH
Specialized tax advisory built for proper execution and ongoing support
SPECIALIZED
Deep expertise in STR tax strategy for real estate investors
Not a generalist practice. Dedicated focus on the strategies that matter for short-term rental investors.
SPECIALIZED
Deep expertise in STR tax strategy for real estate investors
Not a generalist practice. Dedicated focus on the strategies that matter for short-term rental investors.
SPECIALIZED
Deep expertise in STR tax strategy for real estate investors
Not a generalist practice. Dedicated focus on the strategies that matter for short-term rental investors.
DIRECT
You work directly with your CPA throughout the engagement
No handoffs to junior staff. Direct access and clear communication at every step.
DIRECT
You work directly with your CPA throughout the engagement
No handoffs to junior staff. Direct access and clear communication at every step.
DIRECT
You work directly with your CPA throughout the engagement
No handoffs to junior staff. Direct access and clear communication at every step.
DEFENSIBLE
Every strategy is built to withstand scrutiny
Proper documentation, entity structure, and audit-ready records from day one.
DEFENSIBLE
Every strategy is built to withstand scrutiny
Proper documentation, entity structure, and audit-ready records from day one.
DEFENSIBLE
Every strategy is built to withstand scrutiny
Proper documentation, entity structure, and audit-ready records from day one.
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SERVICES
Comprehensive STR tax advisory from planning through compliance
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Tax Strategy & Planning
We analyze your situation, model potential tax savings, and determine whether the STR strategy fits your goals. Includes material participation assessment and pre-acquisition guidance.
STRATEGY
PLANNING
ANALYSIS
FEASIBILITY
Tax Strategy & Planning
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STR Tax Blueprint
Your complete implementation roadmap—entity structuring, cost segregation coordination, material participation planning, and documentation systems built for your specific situation.
IMPLEMENTATION
ENTITY
TIMING
COST SEG
STR Tax Blueprint
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Ongoing Advisory
Quarterly reviews, material participation tracking, and direct access to your CPA as your portfolio grows. Stay compliant and optimize year over year.
ADVISORY
COMPLIANCE
SUPPORT
Ongoing Advisory
/ 004
Tax Preparation
Annual return preparation for STR investors. Proper reporting of your strategy with audit-ready documentation.
RETURNS
FILING
DOCUMENTATION
market
Tax Preparation
/ 001
Tax Strategy & Planning
We analyze your situation, model potential tax savings, and determine whether the STR strategy fits your goals. Includes material participation assessment and pre-acquisition guidance.
STRATEGY
PLANNING
ANALYSIS
FEASIBILITY
Tax Strategy & Planning
/ 002
STR Tax Blueprint
Your complete implementation roadmap—entity structuring, cost segregation coordination, material participation planning, and documentation systems built for your specific situation.
IMPLEMENTATION
ENTITY
TIMING
COST SEG
STR Tax Blueprint
/ 003
Ongoing Advisory
Quarterly reviews, material participation tracking, and direct access to your CPA as your portfolio grows. Stay compliant and optimize year over year.
ADVISORY
COMPLIANCE
SUPPORT
Ongoing Advisory
/ 004
Tax Preparation
Annual return preparation for STR investors. Proper reporting of your strategy with audit-ready documentation.
RETURNS
FILING
DOCUMENTATION
market
Tax Preparation
/ 001
Tax Strategy & Planning
We analyze your situation, model potential tax savings, and determine whether the STR strategy fits your goals. Includes material participation assessment and pre-acquisition guidance.
STRATEGY
PLANNING
ANALYSIS
FEASIBILITY
Tax Strategy & Planning
/ 002
STR Tax Blueprint
Your complete implementation roadmap—entity structuring, cost segregation coordination, material participation planning, and documentation systems built for your specific situation.
IMPLEMENTATION
ENTITY
TIMING
COST SEG
STR Tax Blueprint
/ 003
Ongoing Advisory
Quarterly reviews, material participation tracking, and direct access to your CPA as your portfolio grows. Stay compliant and optimize year over year.
ADVISORY
COMPLIANCE
SUPPORT
Ongoing Advisory
/ 004
Tax Preparation
Annual return preparation for STR investors. Proper reporting of your strategy with audit-ready documentation.
RETURNS
FILING
DOCUMENTATION
market
Tax Preparation
/ 001
Tax Strategy & Planning
We analyze your situation, model potential tax savings, and determine whether the STR strategy fits your goals. Includes material participation assessment and pre-acquisition guidance.
STRATEGY
PLANNING
ANALYSIS
FEASIBILITY
Tax Strategy & Planning
/ 002
STR Tax Blueprint
Your complete implementation roadmap—entity structuring, cost segregation coordination, material participation planning, and documentation systems built for your specific situation.
IMPLEMENTATION
ENTITY
TIMING
COST SEG
STR Tax Blueprint
/ 003
Ongoing Advisory
Quarterly reviews, material participation tracking, and direct access to your CPA as your portfolio grows. Stay compliant and optimize year over year.
ADVISORY
COMPLIANCE
SUPPORT
Ongoing Advisory
/ 004
Tax Preparation
Annual return preparation for STR investors. Proper reporting of your strategy with audit-ready documentation.
RETURNS
FILING
DOCUMENTATION
market
Tax Preparation
Professionalism you can trust
Wakefield Tax operates under the professional and ethical requirements of a licensed CPA. Your information is treated with strict confidentiality at every step.
Ready to get started?
Book a consultation to discuss your situation and see how Wakefield Tax can support your goals.
Learn the strategy
New to STR tax strategy? Download our free educational guide to understand how it works and what's required to qualify.
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Our Process
How we work with STR investors from first conversation through ongoing support
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001
Discover opportunities and define your priorities
Discover opportunities and define your priorities
We analyze your situation, timeline, and goals to identify key opportunities. Our approach combines technical expertise with a clear understanding of your objectives to establish the right path forward.
We analyze your situation, timeline, and goals to identify key opportunities. Our approach combines technical expertise with a clear understanding of your objectives to establish the right path forward.
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002
Design actionable strategies tailored to your needs
Design actionable strategies tailored to your needs
We develop actionable strategies and practical solutions aligned with your vision. Each recommendation is designed to be scalable, implementable and capable of delivering measurable impact across the organization.
We develop actionable strategies and practical solutions aligned with your vision. Each recommendation is designed to be scalable, implementable and capable of delivering measurable impact across the organization.
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003
Deliver measurable results with lasting impact
Deliver measurable results with lasting impact
We implement plans alongside your team, ensuring sustainable results. Our hands-on approach includes support, monitoring and adaptation to embed changes and deliver long-term value.
We implement plans alongside your team, ensuring sustainable results. Our hands-on approach includes support, monitoring and adaptation to embed changes and deliver long-term value.
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Our Expertise
Where strategy, operations and innovation meet measurable results
Strategy
Developing long-term plans that drive sustainable growth
We help companies define clear goals and create actionable roadmaps for success
Strategy
Developing long-term plans that drive sustainable growth
We help companies define clear goals and create actionable roadmaps for success
Operations
Optimizing processes and improving efficiency
We streamline workflows and structures to deliver measurable business results
Operations
Optimizing processes and improving efficiency
We streamline workflows and structures to deliver measurable business results
Innovation
Creating new opportunities and scalable business models
We design and implement innovative solutions to help companies stay ahead
Innovation
Creating new opportunities and scalable business models
We design and implement innovative solutions to help companies stay ahead
Building partnerships that drive growth
Trusted Partner
Collaborative Approach
Lasting Value
We work closely with clients to deliver results efficiently and effectively. By embedding ourselves in their teams, we ensure strategies are actionable, sustainable, and create long-term value across the organization.
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Our Experts
The team driving strategy, innovation and growth
Sofia Martínez
Head of Client
New York
Sofia drives client success by translating strategy into actionable solutions. She has extensive experience in product launches, market expansion, and building cross-functional teams.
Sofia Martínez
Head of Client
New York
Sofia drives client success by translating strategy into actionable solutions. She has extensive experience in product launches, market expansion, and building cross-functional teams.
Sofia Martínez
Head of Client
New York
Sofia drives client success by translating strategy into actionable solutions. She has extensive experience in product launches, market expansion, and building cross-functional teams.
Sofia Martínez
Head of Client
New York
Sofia drives client success by translating strategy into actionable solutions. She has extensive experience in product launches, market expansion, and building cross-functional teams.
Smart solutions, straightforward costs
Transparent pricing for premium consulting services
Final pricing depends on the scope, complexity and duration of the engagement. Contact us for a tailored proposal.
Service Cost
$15,000 – $50,000
Strategic planning and roadmap development
Strategic planning and roadmap development
Operational analysis and process optimization
Operational analysis and process optimization
Business transformation support
Business transformation support
Innovation and growth initiatives
Innovation and growth initiatives
Ongoing advisory and performance monitoring
Ongoing advisory and performance monitoring
Premium consulting services with transparent costs and measurable value
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frequently asked questions
Straightforward answers to help you make informed choices.
What services do you offer?
We specialize in strategic and operational consulting. Our team helps organizations design growth strategies, optimize business processes, implement digital solutions, drive innovation, and manage organizational change.
What types of clients do you work with?
We work with mid-sized and large companies, government agencies, NGOs, and fast-growing startups. Our clients operate across a wide range of industries, including technology, finance, logistics, manufacturing, healthcare, and the public sector.
What makes your approach different?
We combine deep analytics, practical business expertise, and innovative thinking. Our team brings together top-tier academic backgrounds and hands-on experience with global companies, including Fortune 500 brands. We don’t just provide recommendations — we work with you to make them real.
Do you work with international clients?
Yes. We have a global team with offices in London, New York, Berlin, Seoul, Dubai, and Milan. We support projects across Europe, North America, Asia, and the Middle East.
How can we start working with you?
It all begins with a free strategic consultation. We align on your business goals, define the scope of work, and provide a tailored action plan. After that, you’ll receive a clear proposal outlining project phases, timeline, and resources.
How much do your services cost?
Our pricing depends on the scope and complexity of the project. We offer flexible engagement models — from short strategic sessions to full-scale, long-term programs. All fees are transparent and agreed upon upfront.
What services do you offer?
We specialize in strategic and operational consulting. Our team helps organizations design growth strategies, optimize business processes, implement digital solutions, drive innovation, and manage organizational change.
What types of clients do you work with?
We work with mid-sized and large companies, government agencies, NGOs, and fast-growing startups. Our clients operate across a wide range of industries, including technology, finance, logistics, manufacturing, healthcare, and the public sector.
What makes your approach different?
We combine deep analytics, practical business expertise, and innovative thinking. Our team brings together top-tier academic backgrounds and hands-on experience with global companies, including Fortune 500 brands. We don’t just provide recommendations — we work with you to make them real.
Do you work with international clients?
Yes. We have a global team with offices in London, New York, Berlin, Seoul, Dubai, and Milan. We support projects across Europe, North America, Asia, and the Middle East.
How can we start working with you?
It all begins with a free strategic consultation. We align on your business goals, define the scope of work, and provide a tailored action plan. After that, you’ll receive a clear proposal outlining project phases, timeline, and resources.
How much do your services cost?
Our pricing depends on the scope and complexity of the project. We offer flexible engagement models — from short strategic sessions to full-scale, long-term programs. All fees are transparent and agreed upon upfront.
What services do you offer?
We specialize in strategic and operational consulting. Our team helps organizations design growth strategies, optimize business processes, implement digital solutions, drive innovation, and manage organizational change.
What types of clients do you work with?
We work with mid-sized and large companies, government agencies, NGOs, and fast-growing startups. Our clients operate across a wide range of industries, including technology, finance, logistics, manufacturing, healthcare, and the public sector.
What makes your approach different?
We combine deep analytics, practical business expertise, and innovative thinking. Our team brings together top-tier academic backgrounds and hands-on experience with global companies, including Fortune 500 brands. We don’t just provide recommendations — we work with you to make them real.
Do you work with international clients?
Yes. We have a global team with offices in London, New York, Berlin, Seoul, Dubai, and Milan. We support projects across Europe, North America, Asia, and the Middle East.
How can we start working with you?
It all begins with a free strategic consultation. We align on your business goals, define the scope of work, and provide a tailored action plan. After that, you’ll receive a clear proposal outlining project phases, timeline, and resources.
How much do your services cost?
Our pricing depends on the scope and complexity of the project. We offer flexible engagement models — from short strategic sessions to full-scale, long-term programs. All fees are transparent and agreed upon upfront.