Frequently Asked Questions

Wakefield Tax is a specialized CPA firm focused exclusively on short-term rental tax strategy. We work with high-income earners (doctors, tech executives, consultants, and other professionals) who use STR properties as part of their tax strategy.

Our clients are typically high-income earners with $200K or more in combined household income who own or are acquiring short-term rental properties. Whether you're evaluating the strategy for the first time or looking to optimize an existing position, we meet you where you are.

Yes. Thomas E. Wakefield is a licensed CPA serving clients nationwide. All engagements are conducted remotely via video calls, secure document exchange, and encrypted communication.

Specialization enables the depth of expertise required to coordinate these provisions effectively. By focusing exclusively on STR tax strategy, we maintain expertise in the 7-day average stay exception, material participation rules, cost segregation, bonus depreciation, entity structuring, and multi-state compliance. These are the specific provisions that apply to short-term rental investors.

The document request depends on your track (Exploration or Optimization). Typically: most recent two years of tax returns, income documentation (W-2s, K-1s, or paystubs), property details or listing information, and any existing entity documents. A track-specific document checklist is sent at the start of the engagement.

The Exploration Track is designed exactly for this situation. We analyze your income profile, projected STR economics, and potential tax impact to help you evaluate whether the strategy is viable for your specific situation before you commit to a purchase.

You receive a written Assessment Report and a 30-minute delivery call walking through the findings. The report includes an Opportunity Map showing what strategies are available, and if appropriate, a recommendation to move into the STR Tax Blueprint for comprehensive strategy development.

The Assessment is diagnostic: it tells you where you stand and what opportunities exist. The Blueprint is prescriptive: it builds a complete, implementation-ready strategy with entity recommendations, cost segregation coordination, material participation design, multi-year projections, and a sequenced action plan.

Yes. If you engage for an STR Tax Blueprint within 120 days of Assessment delivery, the full $1,000 Assessment fee is applied as a dollar-for-dollar credit toward the Blueprint engagement. The credit is reflected in the Blueprint engagement letter.

No. The Assessment is available for clients who want a focused diagnostic first, but direct-to-Blueprint engagement is available for clients who already know they need a comprehensive strategy. In direct-to-Blueprint engagements, the diagnostic and analytical work is performed as part of the Blueprint scope at no additional charge.

The base Blueprint price of $5,000 covers a single property (Implementation Track). For clients with multiple properties or entities, the Portfolio Strategy Track is custom-scoped based on your situation. Multi-property pricing follows a structured framework: $5,000 base + $2,000 per additional property + $500 per additional state jurisdiction.

50% deposit at engagement signing, with the remaining balance due upon Blueprint delivery. For a single-property engagement, that is $2,500 at signing and $2,500 upon delivery. Clients with a prior Assessment credit pay the reduced balance on the same 50/50 split.

The completed Blueprint is delivered via secure document exchange, followed by a 60-minute delivery walkthrough via video call. The walkthrough covers every section, answers your questions, and establishes the implementation sequence. You also receive a Material Participation Documentation Kit customized for your situation.

The Blueprint includes a detailed implementation roadmap. For ongoing oversight, including quarterly strategy reviews, material participation monitoring, and proactive tax law updates, clients typically move into the STR Tax Advisory. Tax return preparation is available as a separate engagement.

Each quarterly review is a scheduled strategy call assessing your tax position, material participation status, and any strategic adjustments needed. The Q4 review is a dedicated year-end planning session to finalize deduction timing, expense acceleration, and any year-end actions. You also receive a mid-year tax projection during Q3.

Tax return preparation is a separate engagement available alongside the Advisory. This allows clients to select the specific services that match their needs. Advisory clients who also engage for Tax Preparation benefit from seamless coordination between strategy and compliance.

You have direct email access to your CPA for STR tax strategy questions related to your engaged properties. Acknowledgment within two business days, with substantive responses within three business days. Complex questions requiring research may take longer, with a timeline communicated upon acknowledgment.

The Advisory operates on a month-to-month basis at $500 per month. Either party may terminate with 30 days' written notice. Monthly billing is due on the 1st of each month.

STR returns require specialized knowledge of non-passive activity classification, cost segregation depreciation schedules, material participation documentation, multi-state filing obligations, and entity-level return coordination. STR returns involve specialized provisions that require focused expertise to apply correctly.

Individual return (Form 1040) with STR activity for one property: $1,500–$2,500. Each additional STR property on the individual return: +$1,000. Entity returns (Form 1065 or 1120-S): $1,500–$2,500 per entity. Additional state returns: +$250–$500 per state. A specific fee is quoted in the engagement letter based on your complexity.

Returns are typically delivered within 15–20 business days from receipt of all required documents, subject to filing season volume and complexity. During peak filing season (March through April 15), delivery timelines may be extended. If an extension is necessary, it is filed at no additional charge.

The Advisory provides year-round strategic oversight (quarterly reviews, material participation monitoring, mid-year projections, and year-end planning) that complements tax return preparation. For STR owners who want ongoing professional guidance beyond annual filing, the combination provides comprehensive support.

Monthly transaction categorization for STR income and expenses, bank and credit card reconciliation, monthly profit and loss statement by property, STR platform data integration (Airbnb, VRBO), sales and occupancy tax tracking, year-end financial package for tax preparation, and 1099 preparation support for qualifying contractors.

Bookkeeping is priced at $200–$300 per month per property based on transaction volume and complexity. A specific monthly fee is confirmed during onboarding based on the number of accounts and typical monthly transaction count.

The monthly profit and loss statement by property is delivered by the 15th of the following month, contingent on timely client responses to categorization questions.

You complete the online intake quiz, which takes about 90 seconds. Based on your answers, you receive a preliminary recommendation and pricing. If it looks like a fit, you submit a brief application with additional details. We review it and schedule a 30-minute strategy call to confirm the recommendation, discuss your situation, and determine the right engagement.

Assessment: $1,000 paid in full at engagement signing. Blueprint: 50% deposit at signing, 50% upon delivery. Advisory: $500/month, billed on the 1st of each month. Tax Preparation: paid in full at engagement signing. Bookkeeping: monthly billing, due on the 1st. All payments are processed electronically.

We use secure, encrypted channels for all document exchange, deliverable access, and communication. Access credentials are provided at the start of every engagement.

Yes. Each service is available independently or in combination. Clients select the services that match their needs. There are no required bundles. Most clients who complete a Blueprint engage for the Advisory and Tax Preparation for ongoing support.

When Wakefield Tax builds the strategy through the STR Tax Blueprint and prepares the tax return, we stand behind every position taken on that return. If the STR portion of your return is examined by the IRS, you receive 10 hours of audit representation at no additional cost. The Examination Support commitment applies when both the Blueprint and return preparation are engaged through Wakefield Tax. It does not apply to standalone tax preparation without a Blueprint engagement.

Yes. Some clients engage Wakefield Tax for strategy work (an Assessment or Blueprint) while retaining their current CPA for general filing. Others transition their full tax work. Either arrangement is accommodated. The engagement letter defines the specific scope. For clients who want seamless coordination between strategy and filing, having Wakefield Tax handle both is typically more efficient.