Winnipeg, Manitoba · Real Journey · Real Numbers

My real estate investing journey in Winnipeg.

I'm Jorge Avilan. I moved from Vancouver to Winnipeg with no job, no friends, and no savings. I'm not here to sell you a course or pretend I'm already a guru. This site is my diary: the wins, the losses, the numbers, and the Winnipeg professionals who are helping me turn a duplex into a portfolio that one day funds schools and dignified housing in South America.

Read My 6-Month Case Study Connect with My Team

$0: Housing cost/mo
5%: Down (CMHC)
2: Units First duplex

Jorge Avilan in front of his Winnipeg duplex

The First Deal

Character duplex · Winnipeg core

Purchased with 5% CMHC down. Unit 2 rent covers PITI.

The Playbook

Three moves to your first Winnipeg house hack.

Every step below is what I actually did — no theory, no gurus.

Multifamily 101

Learn how to live for free by letting tenants pay your Winnipeg mortgage.

Creative Financing

How to use rental offset rules and CMHC insurance to qualify for properties most banks would decline.

Off-Market Scouting

The system for targeting cash-flowing 2-4 unit multiplexes across Winnipeg — before they hit the MLS.

Case Study

The exact numbers of my first duplex.

Illustrative snapshot of month-one operations after tenant placement. Rounded for readability — not tax or investment advice.

See the full breakdown

Monthly snapshot

Purchase price: $379,000
Down payment (5% CMHC): $18,950
PITI + utilities: $2,410
Rent — Unit 2: $1,650
Owner's contribution (Unit 1): $760

The Trust Bridge

I didn't do this alone.

Two Winnipeg pros made this possible. I'm handing you the exact people I trust.

Investor-Focused REALTOR®

Dennis Wiebe

Vivico Real Estate Inc.

Flipper, landlord, and hands-on renovator since 2005. Dennis pressure-tests every deal like the investor he is — furnaces, wiring, cash-flow assumptions.

Meet Dennis

Mortgage Specialist

Terrin Ramsey

Castle Mortgage Group (TMG)

The go-to broker for newcomers, self-employed clients, and house hackers. Specializes in rental offset and CMHC 5%/10% owner-occupied strategies.

Meet Terrin

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Dennis Wiebe is a licensed REALTOR® with Vivico Real Estate Inc. Terrin Ramsey is a licensed Mortgage Specialist with Castle Mortgage Group (TMG The Mortgage Group). All content is for educational purposes only and does not constitute financial, mortgage, legal, or investment advice.