Stessa vs SimplifyEm Landlord Software: 2026 Comparison

• Stessa excels in financial tracking and tax preparation but lacks maintenance management features.
• SimplifyEm offers a broader set of property management tools, including lease drafting and maintenance tracking.
• TenantFlow is optimized for landlords who need a simple way to organize leases, documents, and maintenance requests without payment processing.
• Pricing for all three platforms scales with the number of units, but SimplifyEm has hidden fees that can add up quickly.
• For landlords managing 1–20 units, the best choice depends on whether financial tracking or maintenance management is a higher priority.

Financial Tracking and Tax Preparation for Landlords

Both Stessa and SimplifyEm offer financial tracking features, but they differ in their approach and depth. Stessa is designed with tax preparation in mind, offering features like automatic income and expense categorization, as well as integration with TurboTax. This makes it a good choice for landlords who want to streamline their tax filing process.

For example, Stessa can automatically categorize income from rental payments and expenses like maintenance and repairs. It also provides year-end financial reports that can be used to prepare tax returns. Stessa's interface is intuitive and user-friendly, making it easy for landlords to keep track of their finances throughout the year.

SimplifyEm also offers income and expense tracking, but its features are more basic compared to Stessa. However, SimplifyEm does allow for custom categories and tags, which can be helpful for landlords who have specific tracking needs. SimplifyEm also offers 1099 reporting, which is a useful feature for landlords who work with contractors.

For example, SimplifyEm allows landlords to create custom categories for expenses like advertising, legal fees, and insurance. This can be helpful for landlords who want to track their expenses more closely or who have unique tax situations. SimplifyEm's 1099 reporting feature can also save landlords time and reduce errors when preparing tax forms for contractors.

For landlords who need advanced financial tracking and tax preparation features, Stessa is likely the better choice. However, for those who need more flexibility in their financial tracking and don't mind a more basic feature set, SimplifyEm may be sufficient. Landlords who need to track expenses more closely or who have unique tax situations may also find SimplifyEm's custom categories and 1099 reporting features helpful.

Lease Management and Document Organization for Landlords

Lease management and document organization are critical for landlords, as they need to keep track of leases, addendums, and other important documents. Stessa offers a document storage feature, but it is quite basic and lacks advanced organization tools.

Stessa's document storage feature allows landlords to upload and store documents like leases, addendums, and inspection reports. However, it lacks advanced organization tools like custom categories or tags, which can make it difficult for landlords to keep track of their documents as their portfolio grows.

SimplifyEm, on the other hand, offers more robust lease management features. Landlords can create and send leases directly from the platform, as well as store and organize documents. SimplifyEm also offers e-signature capabilities, which can save time and reduce paper clutter.

For example, SimplifyEm's lease management feature allows landlords to create and send leases directly from the platform. Landlords can also customize their lease templates with their own branding and terms. SimplifyEm's document organization feature allows landlords to create custom categories and tags for their documents, making it easy to find and organize important files. SimplifyEm's e-signature feature also allows landlords to send leases to tenants for electronic signature, which can save time and reduce paper clutter.

TenantFlow offers lease lifecycle management for landlords, including drafting, renewals, terminations and a document vault. This can be helpful for landlords who need to keep track of leases, addendums, and other important documents in one place.

For landlords who need advanced lease management features, SimplifyEm is likely the better choice. However, for those who only need basic document storage, Stessa or TenantFlow may be sufficient. Landlords who want to customize their lease templates or who need advanced document organization tools may also find SimplifyEm's features helpful. TenantFlow is a good fit for landlords who need to manage leases and documents without payment processing.

Maintenance Management for Landlords

Maintenance management is another critical aspect of property management. Stessa does not offer maintenance management features, which can be a dealbreaker for some landlords.

Landlords who use Stessa will need to rely on external tools or spreadsheets to track maintenance requests and repairs. This can be time-consuming and inefficient, especially as a landlord's portfolio grows. Landlords who use Stessa may also find it difficult to communicate with tenants and contractors about maintenance issues, as Stessa does not offer messaging or communication tools.

SimplifyEm offers maintenance management features, allowing landlords to create and track work orders, as well as communicate with tenants and contractors. This can save time and improve efficiency for landlords who manage multiple properties.

For example, SimplifyEm's maintenance management feature allows landlords to create work orders for repairs and track their progress from start to finish. Landlords can also communicate with tenants and contractors about maintenance issues directly from the platform, which can save time and reduce miscommunication. SimplifyEm's maintenance management feature also allows landlords to track expenses related to repairs and maintenance, which can be helpful for tax purposes.

TenantFlow offers maintenance request tracking for landlords. This includes submission, vendor assignment, status updates, photos, and completion timestamps. TenantFlow also offers a seasonal maintenance checklist to help landlords stay on top of property maintenance tasks throughout the year.

For landlords who need maintenance management features, SimplifyEm is likely the better choice. However, for those who don't need these features or already have a system in place, Stessa may be sufficient. Landlords who need to track maintenance expenses for tax purposes or who want to communicate with tenants and contractors more efficiently may also find SimplifyEm's features helpful. TenantFlow is a good fit for landlords who need maintenance tracking and want to use a seasonal maintenance checklist.

Pricing and Fees for Landlords

Pricing is an important consideration for landlords, as they need to balance the cost of software with the value it provides. Stessa offers a free plan, which includes basic financial tracking and document storage features. Paid plans start at $20 per month for up to 15 units, with pricing increasing based on the number of units.

Stessa's free plan is a good option for landlords who are just starting out or who have a small portfolio. The free plan includes basic financial tracking and document storage features, which can be helpful for landlords who want to keep track of their finances and important documents. Stessa's paid plans offer more advanced features like automatic income and expense categorization, as well as integration with TurboTax.

SimplifyEm also offers a free plan, which includes basic property management features. Paid plans start at $25 per month for up to 10 units, with pricing increasing based on the number of units. However, SimplifyEm also charges additional fees for features like e-signatures and 1099 reporting, which can add up quickly.

SimplifyEm's free plan is a good option for landlords who are just starting out or who have a small portfolio. The free plan includes basic property management features like lease management and document storage, as well as maintenance tracking. SimplifyEm's paid plans offer more advanced features like custom categories and tags for expenses, as well as 1099 reporting.

For landlords who need advanced features and are willing to pay for them, SimplifyEm may be worth the cost. However, for those who want a more straightforward pricing structure, Stessa or TenantFlow may be a better choice. Below is a table that compares the pricing of Stessa, SimplifyEm, and TenantFlow.

Features	Stessa (Free)	SimplifyEm (Basic)	TenantFlow (Starter)
Financial Tracking	Yes	Yes	Yes
Document Storage	Basic	Advanced	Basic
Lease Management	No	Yes	Yes
Maintenance Tracking	No	Yes	Yes
Price per Month	$0	$25	$19

Scalability for Landlords

As landlords grow their portfolios, they need software that can scale with them. Stessa's paid plans support up to 150 units, which should be sufficient for most independent landlords. SimplifyEm's paid plans support up to 50 units, but additional units can be added for an extra fee.

Stessa's paid plans offer more advanced features like automatic income and expense categorization, as well as integration with TurboTax. Stessa's plans also support up to 150 units, which should be sufficient for most independent landlords. Landlords who anticipate significant growth in their portfolios may find Stessa's scalability helpful.

SimplifyEm's paid plans offer more advanced features like custom categories and tags for expenses, as well as 1099 reporting. SimplifyEm's plans also support up to 50 units, but additional units can be added for an extra fee. Landlords who anticipate significant growth in their portfolios may find SimplifyEm's scalability helpful, but they should be aware of the additional fees for extra units.

TenantFlow's Growth plan supports up to 100 units, and the Max plan is unlimited. This makes TenantFlow a good choice for landlords who anticipate significant growth in their portfolios. For tips on scaling your rental business, check out this guide.

TenantFlow's Growth plan offers more advanced features like DocuSeal for e-signatures, as well as premium financial reports. TenantFlow's plans also support up to 100 units, with the Max plan being unlimited. Landlords who anticipate significant growth in their portfolios may find TenantFlow's scalability helpful.

Integration and Automation for Landlords

Integration and automation can save landlords time and reduce errors. Stessa integrates with QuickBooks, TurboTax, and other popular accounting software. SimplifyEm offers integrations with Zillow, Syndication, and other property listing sites.

Stessa's integrations with QuickBooks and TurboTax can save landlords time and reduce errors when preparing tax returns. Stessa's integration with other popular accounting software can also make it easier for landlords to keep track of their finances throughout the year. Landlords who use QuickBooks or TurboTax may find Stessa's integrations helpful.

SimplifyEm's integrations with Zillow and other property listing sites can save landlords time and reduce errors when advertising their properties. SimplifyEm's integration with Syndication can also make it easier for landlords to manage their listings across multiple platforms. Landlords who advertise their properties on Zillow or other listing sites may find SimplifyEm's integrations helpful.

TenantFlow integrates with your e-signature tool for e-signatures and offers a variety of financial reports that can be exported to accounting software. However, TenantFlow does not offer integrations with property listing sites.

TenantFlow's integration with your e-signature tool for e-signatures can save landlords time and reduce paper clutter when sending leases to tenants. TenantFlow's financial reports can also make it easier for landlords to prepare tax returns or share financial information with accountants. Landlords who need e-signature capabilities or who want to export financial reports may find TenantFlow's integrations helpful.

For landlords who need integrations with accounting software, all three platforms offer options. For those who need integrations with property listing sites, SimplifyEm is likely the better choice.

Customer Support for Landlords

Customer support is an important consideration for landlords, as they may need help troubleshooting issues or learning how to use the software. Stessa offers email support and a knowledge base with articles and videos.

Stessa's email support is responsive and helpful, and the knowledge base includes articles and videos that can help landlords learn how to use the software. Landlords who prefer email support or who want to troubleshoot issues on their own may find Stessa's customer support helpful.

SimplifyEm offers phone, email, and chat support, as well as a knowledge base. SimplifyEm's customer support is available 24/7, which can be helpful for landlords who need assistance outside of regular business hours. Landlords who prefer phone or chat support or who want around-the-clock assistance may find SimplifyEm's customer support helpful.

TenantFlow offers email support and a knowledge base with articles and videos. TenantFlow's email support is responsive and helpful, and the knowledge base includes articles and videos that can help landlords learn how to use the software. Landlords who prefer email support or who want to troubleshoot issues on their own may find TenantFlow's customer support helpful.

For landlords who need phone or chat support, SimplifyEm is likely the better choice. For those who prefer email support and a comprehensive knowledge base, Stessa or TenantFlow may be sufficient.

Related reading: Stessa Vs Appfolio Complete Comparison For 2026 and Simplifyem Vs Avail Complete Comparison For 2026 and Simplifyem Pricing: Hidden Fees Revealed.

Free Resources for Landlords

All three platforms offer free resources that can be helpful for landlords. Stessa offers a free seasonal maintenance checklist, which can help landlords stay on top of property maintenance tasks throughout the year. Stessa's free checklist includes tasks like HVAC servicing, plumbing inspections, and exterior maintenance.

SimplifyEm offers a free landlord tax deduction tracker, which can help landlords keep track of deductible expenses throughout the year. SimplifyEm's free tracker includes categories like advertising, legal fees, and insurance, as well as auto-totaled totals for easy tax preparation. Landlords who want to maximize their tax deductions or who need help keeping track of expenses may find SimplifyEm's free tracker helpful.

TenantFlow offers a free security deposit reference card, which can help landlords understand their rights and responsibilities when it comes to security deposits. TenantFlow's free reference card includes information about deposit limits, return deadlines, and required documentation per state. Landlords who want to ensure they are following the law when it comes to security deposits may find TenantFlow's free reference card helpful.

FAQ

Which platform is best for landlords who need advanced financial tracking?

Stessa is likely the best choice for landlords who need advanced financial tracking and tax preparation features. Stessa offers automatic income and expense categorization, as well as integration with TurboTax.

Which platform is best for landlords who need maintenance management features?

SimplifyEm is likely the best choice for landlords who need maintenance management features. SimplifyEm offers work order creation and tracking, as well as communication tools for tenants and contractors.

Which platform is best for landlords who need lease management features?

SimplifyEm is likely the best choice for landlords who need lease management features. SimplifyEm offers lease creation and sending, as well as e-signature capabilities.

Which platform is best for landlords who need to scale their portfolios?

TenantFlow is likely the best choice for landlords who need to scale their portfolios. TenantFlow's Growth plan supports up to 100 units, and the Max plan is unlimited.

Which platform is best for landlords who need integrations with accounting software?

All three platforms offer integrations with accounting software. Stessa integrates with QuickBooks and TurboTax, SimplifyEm offers integrations with Zillow and other property listing sites, and TenantFlow offers financial reports that can be exported to accounting software.

Which platform is best for landlords who need phone or chat support?

SimplifyEm is likely the best choice for landlords who need phone or chat support. SimplifyEm offers 24/7 phone, email, and chat support.

Which platform is best for landlords who need free resources?

All three platforms offer free resources that can be helpful for landlords. Stessa offers a free seasonal maintenance checklist, SimplifyEm offers a free landlord tax deduction tracker, and TenantFlow offers a free security deposit reference card.