Episode 152: Remote Landlord Systems with Sydney Young
Summary
How on earth do you manage rentals two time zones away without a property manager? Easy. Systems and people who you can trust. Okay, it’s not so easy, but the systems part and people you can trust part are BOTH true. Setting up systems for remote landlording can take some doing, but technology is advancing nearly daily and more and more of it is FREE. Business expert Sydney Young joins me on today’s show to talk about how self-managing landlords can set up remote systems and many free resources including www.fillout.com, www.cal.com, and adobe e-sign. (And don’t forget the voice note addition in fillout.com!)
Click Here to View Sydneys Fillout Template!
Listen to the full episode :
This Week’s Blog Post:
How I Manage Properties from 2,500 Miles Away
Hi friends! I’m Dr. Jen, and in this episode of My Life as a Landlord, we’re talking systems—specifically, how to self-manage rental properties remotely. When people find out I live in Hawaii but manage rentals in Canada, their first question is always, “How do you do that?” The answer: I built systems and found people I trust. One of those people is my business and podcast coach, Sydney Young. She joined me in this episode to break down the tools and workflows landlords can implement to streamline tenant placement, communication, maintenance, and more.
Systematizing the Tenant Journey
Sydney started by walking us through the five key phases of the tenant placement process: inquiry, screening, scheduling, signing, and onboarding. She emphasized zooming out to look at the big picture first, then templating each stage so you’re not reinventing the wheel every time. For example, instead of replying to a flood of “I’m interested” messages on Facebook Marketplace, use a digital application form like Zillow or Fillout.com to gather standardized data and pre-qualify leads. It filters out tire kickers and sets the tone for a more efficient rental experience—for both you and the tenant.
Scheduling, Showings, and Smart Tech
One of my favorite tips from Sydney was using Cal.com to let potential tenants schedule showings without back-and-forth messaging. It saves time, especially for remote landlords coordinating with local contacts. She also recommends sending video walkthroughs and floor plans before showings, so applicants can preview the unit and self-select based on what they see. For access, she uses smart locks and lockboxes, which make coordinating maintenance or remote showings a breeze. It’s all about creating repeatable systems that work without you having to be physically present.
Signing Leases and Collecting Rent Remotely
When it’s time to sign, Sydney suggests using fillable PDFs and tools like Adobe Sign for digital lease execution. For collecting rent, we talked about the differences between Canada and the U.S. In Canada, e-transfers are common, but be cautious with auto-deposit if you're still screening tenants. In the U.S., Venmo, Zelle, and direct bank deposits are more typical. Either way, the goal is to automate rent collection as much as possible—and to stop “chasing” payments. Instead, the onus should be on the tenant to pay on time.
Onboarding and Final Tips
To wrap it all up, Sydney recommends creating a templated welcome email for new tenants. Include everything they need: signed lease, payment instructions, emergency contacts, move-in details, parking info, and any manuals. This one-time setup can save you hours with every new lease. Her parting advice? Every time you do something more than once—template it. That’s the secret to running a smooth, scalable rental business, whether you’re across town or across the ocean.
We recorded this episode from Maui, Hawaii, and Powell River, BC. Why? Because real estate takes you places. Where do you want real estate to take you?
Join me next week for Episode 153, where we get a firsthand update on the Maui wildfire recovery from Planning Director Kate Blackstone. I’ll see you there!