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Real Estate Strategy
Educational articles for real estate investors covering rentals, flips, short-term rentals, tax planning, cash flow, financing, deal analysis, entity structure, and how real estate decisions may fit into a broader financial plan.


Airbnb vs. House Flip: A Real Estate Investment Case Study
A real world investment property analysis showing how financing costs, operating expenses, and cash flow projections can change an investor’s strategy. By Kendall Maccagnan, CPA, CFP® and Financial Advisor in Tampa, Florida Adaptation in Real Estate This case study is based on an actual investment property analysis and details have been rounded and simplified for educational purposes. An investor purchased an investment property initially thinking they would rent it through A
kendallmaccagnan
Jun 244 min read


Real Estate Professional Status (REPS): How to Qualify, What Counts, and What the IRS Expects
Learn how real estate professional status (REPS) works, including qualification rules, material participation requirements, and documentation expectations. Understand when rental losses may be treated as nonpassive and how the IRS evaluates eligibility. By Kendall Maccagnan, CPA, CFP® and Financial Advisor in Tampa, Florida Key Takeaways Rental real estate is generally treated as a passive activity unless specific requirements are met To qualify for REPS you must spend more t
kendallmaccagnan
May 205 min read


What is a Cost Segregation Study and Should Real Estate Investors Consider One?
Cost segregation studies may help real estate investors accelerate depreciation, increase early tax deductions, and improve cash flow. Learn how they work, who benefits most, and key considerations including bonus depreciation and recapture. By Kendall Maccagnan, CPA, CFP® and Financial Advisor in Tampa, Florida Key Takeaways Cost segregation studies may allow certain building components to be depreciated over shorter recovery periods, accelerating tax deductions. Larger upfr
kendallmaccagnan
Apr 226 min read


2026 Tax Changes for Real Estate Investors: Key OBBBA Updates and Planning Opportunities
Learn key OBBBA tax changes for real estate investors including bonus depreciation, QBI updates, business interest deductions, Opportunity Zone changes, and estate planning strategies. By Kendall Maccagnan, CPA, CFP® and Financial Advisor in Tampa, Florida Key Takeaways 100% bonus depreciation is restored under current law, which may allow real estate investors to accelerate deductions on qualifying property through cost segregation strategies The Section 163(j) interest lim
kendallmaccagnan
Apr 157 min read
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