How Walter Woodford finally found the right software after 42 years

A lifetime in real estate, and still searching for the right software

After more than four decades in real estate, Walter Woodford had tried nearly every property management system the industry produced. None of them fit the way he worked. They were cluttered with features he didn’t need, missing the ones he did, or too complicated to use day-to-day.

His business had evolved into a hybrid model—part short-term rental management, part mortgage payment servicing—and most software simply wasn’t built for that. The result was a slow, friction-heavy workflow that required more people, more oversight, and more manual handling than it should have.

What made it difficult wasn’t just the inefficiency. It was the quiet frustration of knowing that after decades in the business, none of the tools he tried had ever made management easier.

“Over the 42 years I’ve been in business, I’ve tried almost everything. I had many applications I didn’t use in those other [programs].”

Walter didn’t need bells and whistles. He needed something that worked—cleanly, intuitively, and without slowing him down.

Guided onboarding, clear tutorials, and software built on simplicity

Walter found DoorLoop through a simple internet search. Immediately, things made sense. The onboarding videos were informative, the interface was user-friendly, and the support team made the process feel possible, even after years of trying tools that didn’t fit.

Every time he added a new module—mortgages, short-term rentals, payment tracking—the team was there, answering questions, building his confidence, and helping him understand each piece before moving to the next.

“They did a lot of handholding along the way. It was the support staff that [showed me] I could do this.”

And for the first time, Walter found software where the features he needed—not the ones he didn’t—finally aligned with the way he ran his business.

Less administration, more opportunity

The biggest transformation in Walter’s workflow came from automating mortgage and rental payments. What once required manual tracking, reminders, bank deposits, and administrative oversight was suddenly handled by DoorLoop—accurately and consistently.

“DoorLoop completely replaced tracking and receiving [payments] and putting [them] in the right bank account.”

The time savings were immediate with Walter gaining at least half a day back each week. For someone managing both short-term rentals and mortgage payments, the software created room for growth in addition to convenience. It unlocked possibilities he hadn’t had time for before: expanding his lending portfolio, experimenting with short-term loans, and scaling his business in ways that once felt out of reach.

“It has given me a future of scalability. I want to do more things now that this piece has been solved.”

After 42 years, Walter had finally found software that felt like it was built for him.