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Read more about the article How STR Bypass Passive Loss Rules

How STR Bypass Passive Loss Rules

  • Post author:Stephen Twomey
  • Post published:September 18, 2026
  • Post category:Passive Income/Real Estate

Short-term rentals have become one of the most discussed tax strategies in real estate investing. The reason is simple. Under specific conditions, STR bypass passive loss rules and allow investors…

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Read more about the article Material Participation Tests Explained: A Guide for Accredited Investors

Material Participation Tests Explained: A Guide for Accredited Investors

  • Post author:Stephen Twomey
  • Post published:September 18, 2026
  • Post category:Accredited Investors

Understanding material participation tests is critical for investors navigating passive activity loss rules. Under IRS Section 469, your ability to deduct losses depends on whether you are materially involved in…

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Read more about the article What Qualifies as Short Term Rental for Tax Purposes

What Qualifies as Short Term Rental for Tax Purposes

  • Post author:Stephen Twomey
  • Post published:September 17, 2026
  • Post category:Real Estate

Short-term rentals have reshaped real estate investing and generated new tax complexities for owners. Understanding how the IRS defines qualifying activity is essential for investors optimizing tax outcomes. What Qualifies…

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Read more about the article 401(k) Tax Benefits: How They Work and How to Maximize Them

401(k) Tax Benefits: How They Work and How to Maximize Them

  • Post author:Stephen Twomey
  • Post published:September 17, 2026
  • Post category:401K

The 401(k) tax benefits available to American workers can reduce current taxable income, defer taxes on investment growth, and potentially provide tax-free retirement withdrawals through Roth contributions. For accredited investors…

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Read more about the article Short Term Rental Tax Benefits: A Strategic Investor’s Guide

Short Term Rental Tax Benefits: A Strategic Investor’s Guide

  • Post author:Stephen Twomey
  • Post published:September 16, 2026
  • Post category:Investor Guide

Short term rental tax benefits have become a major reason high-income investors enter the STR market. These properties can generate cash flow while offering meaningful tax efficiency when structured correctly.…

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Read more about the article Does Contributing to a 401(k) Reduce Taxable Income?

Does Contributing to a 401(k) Reduce Taxable Income?

  • Post author:Stephen Twomey
  • Post published:September 16, 2026
  • Post category:401K

Yes, contributing to a traditional 401(k) generally reduces your current federal taxable income because contributions are made on a pre-tax basis. A Roth 401(k) works differently because contributions are made…

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Read more about the article Exit Strategy Tax Impact Real Estate: What Investors Must Know

Exit Strategy Tax Impact Real Estate: What Investors Must Know

  • Post author:Stephen Twomey
  • Post published:September 15, 2026
  • Post category:Real Estate

Real estate investors often focus on acquisition and cash flow. However, the exit strategy tax impact real estate investors face ultimately determines their net return. A profitable sale can become…

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Read more about the article Real Estate Recordkeeping Best Practices for Investors

Real Estate Recordkeeping Best Practices for Investors

  • Post author:Stephen Twomey
  • Post published:September 15, 2026
  • Post category:Real Estate

Real estate recordkeeping best practices are not just about staying compliant with the IRS. They are about building an infrastructure that supports scale, protects capital, and improves financial clarity. Serious…

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Read more about the article Are Investment Advisory Fees Deductible in 2026?

Are Investment Advisory Fees Deductible in 2026?

  • Post author:Stephen Twomey
  • Post published:September 11, 2026
  • Post category:Investment Management/Tax Law

Are investment advisory fees deductible in 2026? For most individual investors, the federal answer is no. Fees paid for ordinary portfolio management, financial advice, and investment management generally cannot be…

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Read more about the article Depreciation Recapture 1099: A Guide for Accredited Investors

Depreciation Recapture 1099: A Guide for Accredited Investors

  • Post author:Stephen Twomey
  • Post published:September 11, 2026
  • Post category:Accredited Investors

Depreciation recapture affects investors who sell assets they previously depreciated. It determines how the IRS taxes gains and how you report them. In this guide we explain the rules, reporting…

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