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Stessa Tax Features: Complete Guide for Landlords (2025)

Stessa is popular for rental property tracking, but how well does it handle taxes? We break down every tax-related feature, its limitations, and what you might be missing.

Key Takeaway

Stessa excels at basic expense tracking but lacks critical tax features like 1099 generation, AI tax optimization, credit card sync, and year-end planning. For landlords focused on minimizing taxes, dedicated tax software saves significantly more than it costs.

Complete Tax Feature Breakdown

Income & Expense Tracking

Basic categorization of rental income and expenses. Manual entry or bank sync.

Limitation: No credit card sync - must manually enter Home Depot, repair expenses, etc.

Bank Account Sync

Connect checking accounts via Plaid for automatic transaction import.

Limitation: Only bank accounts, not credit cards where most landlord expenses occur.

Schedule E Report

Generate a basic Schedule E report showing income and expenses by category.

Limitation: No AI review or optimization suggestions. Manual verification required.

1099 Generation

Not available in Stessa.

Limitation: Must use separate software or paper forms for contractor 1099s.

Tax Optimization Insights

Not available in Stessa.

Limitation: No proactive suggestions to reduce tax burden or year-end planning.

Depreciation Tracking

Basic depreciation calculation based on purchase price.

Limitation: No cost segregation insights or bonus depreciation optimization.

Year-End Tax Planning

Not available in Stessa.

Limitation: No alerts for tax-saving opportunities before year-end.

Quarterly Tax Estimates

Not available in Stessa.

Limitation: Must calculate estimated taxes manually or use other software.

What This Means for Your Taxes

Missed Deductions

Without credit card sync and AI insights, landlords typically miss $500-2,000 in legitimate deductions annually. Manual entry is tedious and error-prone.

1099 Compliance Risk

Failing to file 1099s for contractors can result in $50-270 penalties per form. Stessa doesn't generate these, leaving you exposed.

No Tax Planning

Year-end tax planning can save $1,000-5,000 by timing expenses correctly. Stessa provides no proactive alerts or suggestions.

Basic Depreciation

Cost segregation can accelerate $10,000-50,000 in deductions. Stessa only tracks basic straight-line depreciation.

A Better Alternative for Tax-Focused Landlords

LandlordTax.tech: Built for Tax Optimization
  • Credit card sync - Capture all expenses automatically
  • AI tax insights - Proactive savings suggestions
  • Unlimited 1099s - Stay compliant effortlessly
  • Year-end planning - Alerts before Dec 31
  • Cost segregation - Maximize depreciation
  • $9/month - All features included
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Frequently Asked Questions

Can Stessa generate my Schedule E?
Yes, Stessa can generate a basic Schedule E report that summarizes your rental income and expenses by category. However, it doesn't provide AI review or optimization suggestions. You'll need to manually verify all entries and may miss deductions that tax-focused software would catch.
Does Stessa file 1099 forms for contractors?
No, Stessa does not offer 1099 generation. If you pay contractors (plumbers, electricians, property managers) $600+ annually, you'll need separate software like Tax1099.com or paper forms. LandlordTax.tech includes unlimited 1099 generation.
Why doesn't Stessa sync credit cards?
Stessa focuses on bank account integration for rent collection visibility. However, most landlord expenses (Home Depot, repairs, supplies) go on credit cards. This means manual entry for a significant portion of your deductions, increasing the risk of missed expenses.
Is Stessa good enough for tax filing?
Stessa is adequate for basic income/expense tracking but lacks advanced tax features. If you file your own taxes or work with a CPA, you'll benefit from software with AI tax insights, 1099 generation, and year-end planning alerts.
What's the best alternative to Stessa for taxes?
LandlordTax.tech is designed specifically for tax optimization with AI insights, 1099 generation, credit card sync, and proactive year-end planning. At $9/month, it costs less than the tax savings from one AI suggestion.

Ready for Better Tax Features?

Stessa is great for basic tracking, but if taxes are your priority, you need software built for tax optimization.

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14-day free trial • No credit card required • Import Stessa data easily

Stessa Tax Features: Complete Guide for Landlords (2025) | LandlordTax.tech | LandlordTax - 让DIY房东轻松搞定Schedule E报税