Overview of One Rental Property Saved Me From My 100-Hour Workweeks
This Real Estate Rookie episode features Elijah Ray, a Portland, Oregon investor who used extreme discipline, creative house hacking, and hands-on renovations to escape a 100-hour-per-week grind. At 26, Elijah bought a single-family home, converted part of it into a rental unit, lived in a tiny house in the backyard, and used rental income to reduce his workload and build a path toward financial and personal freedom. The conversation is honest about the upside of house hacking, but it also digs into the messy realities: bad tenant screening, an eviction, awkward landlord-family dynamics, and the realization that being an on-site landlord was not the long-term life he wanted.
Deal Breakdown
Purchase and financing
- Bought his first property in Portland in 2023 at age 26.
- Purchase price: $333,000
- Down payment / cash to close: about $13,000
- Financing: a 1% down Rocket Mortgage program, but with a 7.5% interest rate
- Because it was a single-family home, he could not count rental income toward qualification.
How he made the property work
- He identified a rear section of the house that could be converted into a separate unit.
- He planned the house hack from the start, looking for:
- garages
- basements
- attics
- odd back rooms with separate access
- The rear unit eventually became a rentable space with its own kitchen and bathroom.
- He bought a tiny house / old food cart for about $1,000 and parked it in the backyard so he could live onsite while renting out the main house.
How He Got the Capital
The grind before buying
- Elijah worked two jobs and was effectively on a 100-hour workweek.
- He used that period to build savings and hit the income level he needed for the purchase.
- He was also paying down debt during that time, including:
- a car purchase
- a $13,000 surgery bill
Motivation
- His motivation came less from “chasing success” and more from wanting to avoid a life he didn’t want.
- Seeing people around him stuck in jobs and lifestyles they didn’t like pushed him to keep going.
- He stayed focused by working backward from goals and checking them weekly.
Renovations, House Hacking, and Tenant Income
Initial rental setup
- He funded early renovations partly with credit cards.
- Bathroom work alone cost around $6,000.
- A YouTube video about his journey helped him connect with a local renter before the unit was even fully finished.
First tenant
- First tenant paid $1,200/month, covering nearly half the mortgage.
- Mortgage was around $2,550/month.
- Later he raised rent to $1,350/month because utilities were costing too much.
Tiny house phase
- He eventually lived in the tiny house in the backyard.
- That arrangement allowed:
- one tenant in the house
- his sister to live in the other space temporarily
- him to live onsite without paying rent
Eviction and Hard Lessons
What went wrong
- He rented to a couple who:
- had no jobs
- showed what looked like a fake bank screenshot
- had poor credit
- paid no deposit
- He admitted he was desperate to fill the unit, which caused him to overlook red flags.
- The tenant situation ended in an eviction process and court involvement.
What he learned
- Don’t rush to place the first applicant.
- Verify income and documentation carefully.
- Don’t rely on screenshots or informal trust.
- Use a more professional system for:
- tenant screening
- lease administration
- rent collection
- communication
Eviction reality check
- Evictions are emotionally draining, especially when you live onsite.
- He learned the legal process is highly specific and requires proper steps.
- He also noted that landlord assistance resources may exist locally, but he didn’t research them enough at the time.
Renting to Family
Sister as a tenant
- Elijah’s sister lived in the property with her kids for a period.
- This was mostly positive because:
- they communicated well
- she helped financially and physically with renovations
- she paid in advance
- The biggest downside was lack of privacy and the stress of living so close to family.
Family rental takeaway
- Renting to family can work if:
- communication is strong
- expectations are clear
- money and repairs are handled professionally
- Even good family arrangements can still feel emotionally complicated.
Tools and Systems He Used
- Zillow for tenant screening later on
- Early on, he used very informal methods:
- screenshots of credit scores
- screenshots of bank balances
- text-message communication
- He eventually realized he needed a more professional setup and considered property management software and/or a management company.
Why He Stopped Being a Landlord
The pivot
- After the eviction and the stress of living onsite with tenants, Elijah realized he no longer wanted the house-hacking lifestyle permanently.
- He sold the tiny house and moved back into the main home.
- He is now turning the property into his own dream home rather than keeping it as a rental.
Bigger life decision
- He also quit his job about nine months earlier and is going all-in on YouTube.
- Real estate, for him, was not just about cash flow — it was a bridge that created time and flexibility for content creation.
Key Takeaways for Rookie Investors
House hacking can work, but it’s not passive
- Elijah’s story shows that house hacking can dramatically reduce housing costs.
- But it also comes with:
- repairs
- tenant issues
- emotional strain
- a lot of labor
Screening matters more than urgency
- His biggest mistake was letting desperation override judgment.
- A strong rental deal can still become a bad experience if tenant screening is weak.
Real estate can fund other goals
- The property gave him time, leverage, and flexibility to pursue YouTube.
- His main message: real estate doesn’t have to be forever — it can be a stepping stone.
On-site landlording may not be for everyone
- Living next to tenants and family members created awkwardness.
- Elijah ultimately realized he prefers not to live onsite if he invests again.
Future Plans
- He still likes real estate and sees it as part of his long-term plan.
- But his future strategy looks different:
- possibly Airbnbs in major cities
- possibly a larger apartment complex
- ideally not living onsite with tenants
- He also learned about the short-term rental tax loophole and was excited by the idea of using it later.
Notable Insight
“Real estate gave me the opportunity to pursue my passion, not just survive my job.”
He repeatedly emphasized that the win was not just financial freedom, but time freedom and the chance to build a life that actually fits him.