About the Firm
One specialty. One client type. One standard.
Wakefield Tax is a specialized CPA firm built exclusively around short-term rental tax strategy for high-income earners.
Wakefield Tax exists because STR tax strategy requires a level of specialization that general-practice firms are not structured to provide.
The provisions that make short-term rental ownership a viable tax strategy (cost segregation, material participation, bonus depreciation, entity structuring, multi-state compliance) each require focused expertise. Handled correctly by a specialist, they function as a coordinated system. Specialization enables focused expertise across every provision that applies to STR investors.
Every service, deliverable, and process at Wakefield Tax is designed specifically for this client type and this strategy. Not as a specialty line within a broader firm, but as the entire firm.
Wakefield Tax is a specialized CPA firm serving clients nationwide. All engagements are conducted remotely via secure document exchange, encrypted communication, and video conference.
Who We Work With
Clients are typically high-income earners (physicians, executives, consultants, and dual-income households) with $200K or more in combined household income who own or are acquiring short-term rental properties. Whether evaluating the strategy for the first time or looking to optimize an existing position, engagements are structured to meet the client where they are.
How We Operate
The approach
Specialization
Every service, deliverable, and process is designed specifically for short-term rental tax strategy. Depth in one area rather than breadth across many.
Direct access
You work directly with the CPA who builds your strategy and oversees your tax position. No handoffs and no support queues.
Defined scope
Every engagement has a clear deliverable, timeline, and price established before work begins. No hourly billing, no scope ambiguity, no surprise invoices.
Outcome orientation
Proactive strategy over reactive compliance. The firm is designed to shape tax decisions in advance, not document them after the fact.
Compliance-first
Every position taken is defensible under examination. Aggressive interpretation is never the approach. Thorough documentation and proper application of the tax code is.
Responsiveness
Defined response windows for every communication channel. Acknowledgment within two business days, substantive responses within three. You always know where things stand.
The CPA
Thomas E. Wakefield, CPA
Wakefield Tax is led by Thomas E. Wakefield, a licensed CPA who built the firm specifically around STR tax strategy. Every strategy, deliverable, and client engagement is handled directly.
Before founding Wakefield Tax, Thomas worked in the tax practice of a top-10 national accounting firm, where he gained deep experience across complex tax engagements serving high-net-worth individuals and businesses. He left to build a firm focused exclusively on what he saw as an underserved niche: STR tax strategy for high-income earners who need specialist-level execution from day one.
Thomas works exclusively with high-income earners who use short-term rental properties as part of their tax strategy. The focus on a single client type and a single area of tax law allows for the depth of expertise that general-practice firms are not structured to provide.
Credentials
Professional standards
Licensed CPA
Active CPA license issued by the Illinois Department of Financial and Professional Regulation.
Treasury Circular 230
Practice before the IRS governed by federal standards for tax practitioners.
AICPA Standards
All engagements conducted under AICPA Code of Professional Conduct and Statements on Standards for Tax Services.
Nationwide Service
Remote practice serving clients in all 50 states with secure, encrypted communication channels.
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