Category: Real Estate (Agents & Investors)

June 10, 2026

Tax Planning at Fortitude: Why We Don’t Do It Like Most Firms

Real Estate (Agents & Investors), S-Corps & Business Structure, Tax Planning, Tax Prep & Filing, Therapists (Private Practice)

Tactical. Practical. Efficient. At Fortitude Tax & Accounting, these three words guide nearly everything we do. As business owners ourselves, we understand that time, cash flow, and attention are limited resources. Our clients don’t need more reports, more meetings, or more complexity. They need clear guidance, practical recommendations, and enough time to take meaningful action….

Read More

December 9, 2025

Do Realtors Need to Issue a 1099? A Clear IRS Guide

Payroll & Contractors, Real Estate (Agents & Investors), Tax Prep & Filing

Whether you work solo, on a team, or lead your own real estate business, the IRS views you as a business owner. That means you must follow the same 1099 rules as any other independent professional. Every year, realtors miss required 1099 filings because they: Assume the brokerage handles it Don’t realize which vendors need…

Read More

December 8, 2025

Organize Your Vendor List for Smooth 1099 Filing Each Year

Bookkeeping & Systems, Payroll & Contractors, Real Estate (Agents & Investors), Tax Prep & Filing

Every January, business owners scramble to collect W-9s, figure out who they paid, clean up payment records, and rush to file 1099s by the deadline. But the truth is simple: 1099 filing is easy when your vendor list is organized year-round. A clean vendor list means: No missing W-9s No guessing who needs a 1099…

Read More

December 7, 2025

Landlords 1099 Requirements Explained: Contractors, Property Managers & More

Bookkeeping & Systems, Payroll & Contractors, Real Estate (Agents & Investors), Tax Prep & Filing

Landlord 1099 Requirements Explained: Contractors, Property Managers & More Landlords operating rental properties are considered business owners, and like any business owner, landlords may need to issue 1099s for certain payments throughout the year. Unfortunately, most landlords don’t learn these rules until tax time, when their CPA asks for contractor totals and W-9 forms. This…

Read More

July 14, 2025

The Complete Landlords Tax Strategy Playbook (2025 Edition)

Real Estate (Agents & Investors)

How to Get Organized, Maximize Deductions, and Build Your Landlords Rental Portfolio with Confidence Whether you’re a first-time landlord or steadily building your portfolio, understanding how rental property taxation really works is essential to keeping more of your profits and avoiding expensive mistakes. At Fortitude Tax & Accounting, we’ve walked landlords through these questions hundreds…

Read More

July 13, 2025

1031 Exchange 101: A Powerful Tax Strategy- When Done Right

Bookkeeping & Systems, Real Estate (Agents & Investors), Tax Prep & Filing

If you’re considering selling a rental property, one of the most powerful tools in your tax strategy toolbox is the 1031 exchange. At Fortitude Tax & Accounting, we help landlords understand how to leverage this tool to keep more of their hard-earned gains working for them—not going to the IRS. Here’s what you need to…

Read More

July 12, 2025

Exit Strategies for Landlords: How to Sell Smarter and Pay Less Tax

Bookkeeping & Systems, Real Estate (Agents & Investors), Tax Prep & Filing

Whether you’re looking to retire, rebalance your portfolio, or cash out on a property at peak value, selling a rental property requires more than a good market and a great listing agent—it requires smart tax planning. At Fortitude Tax & Accounting, we help landlords exit strategically, not emotionally, so they protect their gains and avoid…

Read More

July 11, 2025

Cost Segregation for Landlords: How It Works & Who Should Consider It

Bookkeeping & Systems, Real Estate (Agents & Investors), Tax Prep & Filing

Why OB3 Changes Your Tax Planning in 2025 and Beyond With the passage of the One Big Beautiful Bill Act (OB3), 100% bonus depreciation is back on the table for certain rental property components. This change keeps cost segregation highly relevant for landlords focused on maximizing deductions and long-term planning. At Fortitude Tax & Accounting,…

Read More

July 10, 2025

2025 Tax Law Changes: What They Mean for Your Rentals (OB3)

Bookkeeping & Systems, Real Estate (Agents & Investors), Tax Prep & Filing

With the One Big Beautiful Bill Act (OB3) now signed into law, many landlords are asking: What does this change for my rentals, my tax deductions, and my depreciation strategy? The short answer: Some provisions have been extended, some clarified — and a lot of headlines floating around don’t apply to landlords the way you…

Read More

July 9, 2025

Year-End Checklist for Rental Property Owners: Stay Organized, Save Money, and Be Ready for Tax Time

Real Estate (Agents & Investors), Tax Prep & Filing

Whether you manage one rental property or a growing portfolio, year-end is the perfect time to get ahead of tax season—and stay in control of your business. At Fortitude Tax & Accounting, we help landlords simplify this process and avoid costly mistakes that come from waiting until the last minute. We’re going to assume you’ve…

Read More

Ready to Work Together?

Fortitude Tax & Accounting is led by Melissa Calwell, CPA, EA, with over 30 years of experience helping service professionals including: therapists in private practice, Realtors, and rental property owners make smarter tax decisions.

If you’d like to talk through your situation and see what level of support makes sense, schedule a discovery call with Melissa.