Self-Managing 85 Doors Without Losing Your Mind

✍️ By Debbie Balfour | WBN News |October 15, 2025 | Click HERE for your FREE Subscription to WBN News and/or to be a Contributor.

What if you could self-manage 85 rental units… and still sleep at night?

Sounds crazy, right?
Not for Jamie Flanagan.

Managing a real estate portfolio is no small task, let alone one with more than 85 doors. Yet one investor, Jamie Flanagan, has done just that, without the use of professional property management services.

Flanagan, a full-time investor, entrepreneur, and parent, was recently featured on Let’s Talk Real Estate Investing, where she shared her step-by-step approach to scaling a multi-million-dollar portfolio while maintaining complete operational control. Her story has drawn attention across the investing community for its practical application of systems, automation, and strategic team-building.

“We treat real estate like a business. That changed everything,” Flanagan said during the interview.

Systems Over Stress

Unlike many investors who outsource management once their portfolio reaches a certain size, Flanagan opted to build internal processes that allow her to self-manage efficiently. Using a combination of automation tools, virtual assistants, and a vetted vendor network, she has reduced her workload by over 40 hours per week.

Among the key tactics discussed were:

Creating repeatable systems for tenant communication and maintenance
Hiring skilled tradespeople with expertise in high-cost areas like HVAC
Automating leasing, rent collection, and service requests
Building out standard operating procedures (SOPs) for every stage of property management

Strategic Growth Without Burnout

Flanagan began her investing journey with a single rental property and expanded steadily, focusing on long-term sustainability. One of her first critical decisions was to bypass traditional property managers after early experiences revealed inefficiencies and high costs.

Instead, she developed an internal structure using virtual assistants to handle administrative tasks, while focusing her own efforts on portfolio growth and vendor relations.

“Don’t hire a handyman,” she advised. “Hire a problem-solver with skills in your biggest expense area.”

Lessons for New and Scaling Investors

The episode provides valuable insights for both novice and experienced investors, especially those navigating the challenges of scaling their portfolios without losing control. Topics covered included:

How to build an ideal vendor list from scratch
The most common mistakes self-managing investors make
Strategies for hiring virtual assistants to manage backend tasks
Treating real estate as a business, not a side hustle

Flanagan also discussed how she balances investing with family responsibilities, and how clearly defined processes created both financial and time freedom.

Resources and Community Support

Flanagan and her husband, Brad, also offer resources through their website, bradandjameyflanagan.com.

The couple also hosts a free Facebook group: Brad and Jamie Flanagan – Wealth Through Real Estate, where they share strategies, host discussions, and support aspiring investors.

Listen to the Full Episode

The full interview is available now on YouTube and podcast platforms under Let’s Talk Real Estate Investing.

Debbie Balfour | Real Estate Investing Success Coach + Podcast Host
📍 Website: www.DebbieBalfour.com
📧 Email: Debbie@DebbieBalfour.com
🔗 LinkedIn: Debbie Balfour
▶️ YouTube Channel: youtube.com/@DebbieBalfour

Join the FREE Facebook Group: Let's Talk Real Estate Investing

TAGS: #Real Estate Investing #Time Freedom #Rental Property Systems #Real Estate Podcast # Self-Managing Rentals #VA Automation #WBN TV #WBN News Langley #WBN News Abbotsford #WBN News Okanagan #Debbie Balfour