Jon Armstrong Retires from RT-AFF

Jon Armstrong’s life of adventure, enterprise and resourcefulness has blended strenuous blue-collar labor with street-smart real estate investing and development.

Jon’s unique combination of skills and experience has helped countless homeowners in Northern Virginia during his seven years as Rebuilding Together-AFF’s Director of Programs. He retired in December 2025.

Born in Montreal, Jon’s family lived in Hamilton and Waterdown, Ont., and Vancouver, B.C., before settling in Toronto when he was a teenager. His father, a salesman for a variety of companies, began buying properties and developing small shopping centers and commercial buildings.

While studying for a bachelor’s degree in civil engineering at Queens University in Kingston, Ont., Jon worked summer jobs as a miner in Northern Ontario, drilling a mile underground for iron ore with a “jackleg”—a jackhammer operated horizontally while propped up on a hydraulic leg. He loved the grueling physical labor, which paid well and funded his college expenses.

By his senior year, he was already demonstrating a talent for real estate investing in the planned community of Don Mills being developed near Toronto. With a small downpayment of $3,000-$4,000 and his father’s guarantee on the mortgage, Jon bought planned townhouses pre-construction and resold them before completion, making “a handsome return every time.”

After graduating in 1971, Jon worked another year in the mines before four years working for a management consulting firm, helping Ontario municipal governments manage road construction and maintenance projects. That was followed by a year doing public relations work for a French company mining uranium in northern Saskatchewan.

Jon acquired his real estate license and started buying houses to convert into rental triplexes or fourplexes, using subcontractors for remodeling and construction. When a friend persuaded him to build an addition on his house, the project led to more clients and Jon became a general contractor, specializing in commercial interiors for stores, offices, restaurants and other businesses.

A continental shift

In 1993, in his mid-40s, Jon got restless for new challenges. A friend who had moved to Costa Rica suggested he consider that country. After visiting and researching the country with the help of its business development agency, Jon and his family, with two children then 6 and 8, moved to San Jose.

Within a year, Jon had bought a property large enough to subdivide and build houses. When using subcontractors proved to be unreliable, he hired his own tradesmen, often employing up to 60 workers. Over 24 years, he built more than 65 homes.

In 2017, his wife Abby’s job with Amazon Web Services brought them back to the states, settling in Arlington, Va. Then 68, Jon assumed he was retired but quickly got bored. After meeting a former board member of RT-AFF, Allen Schirmer, he started volunteering for home repair projects. In January 2019, he was hired full-time to replace the retiring director of programs.

With RT-AFF Project Repair Coordinator Fritz Sturz, Jon assessed houses needing major repairs and matched them with corporate and church partners. He helped to schedule, plan and equip their teams of volunteers to work on annual National Rebuilding Day in April and other days throughout the year. In addition to homeowners, beneficiaries include some nonprofit agencies such as Hartwood Foundation, which operates residential services for people with intellectual and developmental disabilities.

Leaving a legacy, looking ahead

Although he had served on a couple charity boards in Toronto, working with RT-AFF “is in many ways the first time I’ve really seriously given back with my time,” said Jon. “It’s hugely impacting.”

Jon encourages others to volunteer with Rebuilding Together, which has affiliates nationwide. If you lack DIY skills, “they’ll put you with a skilled volunteer who love to teach how to put in a handrail or install a grab bar,” he said. “You can pick your projects, most of which are only a half day.”

And a bonus is “the camaraderie—you meet some very interesting people. You never know who you’re standing beside—there are volunteers with some pretty impressive resumes.”

Now retired for a second time, Jon and Abby moved to North Vancouver to live near their daughter Maddy, a solutions architect for a software consulting firm. Their son Austin works in technology sales in London, England.

Jon’s looking forward to hiking, biking and taking up pickleball. And—not surprisingly—he’ll be hiring contractors to renovate the home they purchased.