Hey Everyone! I just realized it’s been 30 years since I moved to Portland. Wow, that feels like a lifetime ago.
In 1996, I graduated from UCSB and moved up to Portland to start a job at Intel. It was a golden era for us (me and Intel). The internet was ramping up, and it was a great time to be a young engineer. All my college friends were able to secure jobs relatively easily. Ahh, what I would give to be 22 again! Life was so much fun when I was young.
It’s a very different story in the age of AI. The job market for recent college grads seems much tighter and more competitive than ever. My son doesn’t even want to study Computer Science because he heard it’s so difficult to get an entry-level position.
The cost of living is also far higher today than it was in 1996. My first apartment cost just $550 a month. I could comfortably afford a one-bedroom apartment on my RCG salary. Even so, because I grew up without much money, I remained frugal. I lived alone for only one year before taking on roommates again to save money.
Today, I’m sharing our 30-year house hacking journey because it is officially coming to an end. Here’s how life changed over three decades.
The Timeline
- 1996: I signed a lease and lived by myself for a year in Beaverton, close to the Intel campus. After sharing a bedroom throughout college to save money, I was tired of roommates and wanted more privacy.
- 1997: Suburban life turned out to be extremely boring for my younger self. I made a lot of friends and decided to move into a two-bedroom apartment in NW Portland with a roommate. That neighborhood was awesome back in the 90s. It was packed with great eateries and cool shops. We lived in an ideal spot to meet up with friends before hitting town on the weekends.
My old apartment building, The Envoy. I think we paid $850 for a 2-bedroom apartment, $425 each. I loved it. Our apartment had hardwood floors, old-timey central boiler radiators (free heat in the winter), and a little office. In retrospect, we should have taken the 3-bedroom penthouse and gotten another roommate. That would have been amazing.


- 1999: After college, Mrs. RB40 joined the Peace Corps and went to Uzbekistan for almost three years. When she returned, she visited me in Portland, and we decided to get back together. We moved into a one-bedroom apartment downtown and got married shortly after. All my friends thought I got her pregnant, but that wasn’t it. We just decided we were better off together.
- 2000: We purchased a 3-bed/2-bath house in Hillsboro to be closer to my work. I figured my bachelor days were over, so I might as well have a shorter commute. The master suite was on the first floor, and there were two bedrooms upstairs. I rented out a bedroom to friends and other new grads while we lived there. Those Intel employees were always at work. It was a pretty good arrangement.
Our old house in Hillsboro. It was way too big for just 2 people.


- 2008: Again, we got tired of the suburbs. We moved to a 2-bed/2-bath condo downtown near Portland State University. Mrs. RB40 went back to get her master’s degree and landed an internship across the river near the Convention Center. My commute got longer, but it made her daily life much easier. We rented out the Hillsboro house.
Our old condo had an awesome view of the Willamette River and Mount Hood.


- 2014: I retired from my engineering career in 2012. After that, it became very annoying to drive to Hillsboro whenever our tenant had an issue. When the tenants moved out, I sold the house and used a 1031 exchange to buy a duplex in my favorite neighborhood, NW Portland.
- 2019: We moved into a unit in the duplex when a tenant left. We wanted a yard for RB40Jr (who was an active 8-year-old), and the area was far more interesting than downtown. The timing was fortunate. A backyard and walkable neighborhood made the extended COVID lockdowns much more bearable. I figured we could take over both units when RB40Jr got older. Our unit only had one bathroom, and RB40Jr slept in the den. It was fine when he was young, but we would need more room when he got older.
- 2026: Our last tenant moved out just in time. RB40Jr is now a 15-year-old teenager who needs more privacy. We also desperately need a second bathroom. Taking over the upstairs unit will double our housing expenses, but we can afford it. We already saved a ton of money over the last 15 years by living in a smaller space. Most families upgrade to a bigger home as soon as a child comes into the picture. The upstairs unit needs a lot of updating, though. Our tenant was there for almost 20 years. It needs new paint, carpet, light switches, power sockets, refrigerator, cabinets, heater, and pretty much everything else.


- 2029: Once RB40Jr leaves for college, we plan to sell the duplex and split our time between California and Thailand. Earlier this year, Mrs. RB40 moved her dad into assisted living and took over his house. These days, she spends a lot of time in CA to help her parents out. As for me, I plan to spend half my time in Thailand. I have a condo in Chiang Mai and a small beach house in Bang Saen. My dad will be 85 by then, and he’ll probably need more help. Hopefully, he can stay healthy and strong for a while.
Wrapping Up
Alright, that’s a wrap for our house hacking journey. We were fortunate to buy into the market when housing was far more affordable, which let us build stability through room rentals and duplexes. That was a good hack. It was also a good idea to stay in a smaller space while our son was young. Mrs. RB40 complained quite a bit, but we made it through. Now, we can finally spread out and enjoy the extra personal space.
What about you? House hacking is much more common these days because housing is so expensive. Are you living creatively?
Joe recommends Empower for DIY investors. They have many useful tools that will help you reach financial independence.
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