In 2025, property managers and landlords alike are relying on software to streamline their operations, automate financial tasks, and prepare for growth. Two recognized platforms—SimplifyEm and Stessa—serve different audiences, but both aim to make managing rentals easier.
So how do they compare? Below, we break down features, pricing, support, and ideal use cases to help you decide which software is the right fit.
SimplifyEm vs Stessa: Feature Comparison Table
Designed to Help You Scale—Starting Small
SimplifyEm is built for both small landlords and mid-sized property managers. Whether you manage 5 units or 500, the system scales with your business. It provides robust tools like accounting, CRM, and automated communications—all without overwhelming you with complexity.
Stessa, by contrast, is purpose-built for individual real estate investors focused on portfolio performance and financial tracking. It’s ideal for landlords who need high-level income/expense insights without managing a large number of tenants.
If you’re a small landlord today, but plan to grow, SimplifyEm is built to grow with you—unlocking features as your portfolio expands without switching platforms.
Ease of Use and Setup
SimplifyEm can be set up in a few minutes. With a streamlined interface and automation baked into everyday workflows, you’ll spend less time in the software—and more time running your business.
Stessa also emphasizes ease of use, especially for tracking property-level finances and preparing for tax season. Its dashboard is tailored to investor metrics, not tenant management.
Pricing Comparison
- SimplifyEm starts at just $25/month with no extra charge for core features like trust accounting, CRM, or support.
- Stessa is free for most users, with optional paid features like rent collection via Stripe, premium banking, or document storage.
Explore SimplifyEm’s pricing here.
Communication & CRM Capabilities
SimplifyEm includes a powerful CRM and Communication Hub to help you:
- Track leads and prospects
- Automate lease renewals and follow-ups
- Send SMS and email reminders
- Keep all conversations in one timeline
While Stessa excels in financial reporting, it doesn’t include built-in communication tools or CRM features.
See how SimplifyEm helps with tenant communication.
Accounting Features
- SimplifyEm offers full General Ledger (GL) accounting, trust fund tracking, bank reconciliation, and owner statements.
- Stessa focuses on financial insights, including income/expense tracking and tax-ready reporting.
For detailed accounting needs and compliance (especially trust accounting), SimplifyEm provides stronger support for those use cases.
Explore SimplifyEm’s accounting capabilities.
Online Rent Collection
SimplifyEm enables rent collection through ACH or credit card, with features like:
- Recurring payments
- Automatic late fee calculation
- Instant ledger updates
Stessa offers rent collection through Stripe integration, which may require setup and processing fees.
Learn more about SimplifyEm’s payment tools.
Customer Support and the “Customer WOW” Experience
One of SimplifyEm’s standout advantages is its live support. Users can get help via:
- Phone
- Chat
- Even tenants can call in for assistance on the tenant portal
This is part of what SimplifyEm calls its “Customer WOW” experience—prioritizing real human help over ticket queues. It’s one of the reasons customers stay loyal.
Stessa offers support via email and a help center designed for self-service, which works well for users comfortable managing everything solo.
Final Verdict: Which One Should You Choose?
Choose SimplifyEm if you:
- Are a small landlord planning to grow
- Need full accounting, CRM, and communication tools
- Value phone support and hands-on help
- Want predictable, affordable pricing
Choose Stessa if you:
- Are an individual investor focused on tracking ROI and property finances
- Prefer a free tool with optional premium add-ons
- Don’t require CRM or in-app communication
For property managers and landlords ready to scale operations and simplify management, SimplifyEm is the best long-term partner.
FAQ (Frequently Asked Questions) SimplifyEm Stessa Comparison
- Is SimplifyEm good for small landlords too?
Yes! SimplifyEm is perfect for small landlords who want to scale, offering powerful tools without complexity.
- Does Stessa have built-in tenant communication?
No, Stessa does not include CRM or messaging tools. Communication must be handled externally.
- Can tenants call SimplifyEm for help?
Yes! Tenants can call SimplifyEm for assistance with their portals—part of their Customer WOW support model.
- Is SimplifyEm easier to scale with than Stessa?
Yes. SimplifyEm is designed to grow with you, with features that unlock as your portfolio expands.
- Is rent collection available on both platforms?
Yes. SimplifyEm offers built-in rent collection, while Stessa offers it through Stripe integration.
Sources:
U.S. Small Business Administration – Rental Property Management Guide
https://www.sba.gov/blog/how-manage-residential-rental-property
HUD – Resources for Landlords and Property Managers
https://www.hud.gov/program_offices/housing/mfh/hsgrent
