By Kyle Gordon, March 31, 2025
Hey there – offering you a snapshot of the way my brain thinks through whether a property will get me one step closer or further away from my personal real estate and financial goals. This is not financial advice and I am not a financial advisor. 
I am a real estate broker in Portland, OR who also invests in real estate, and I consider myself to be part of the FIRE (Financial Independence, Retire Early) movement because I want to give myself more time-freedom to work on things that fill my cup, regardless of how much those things are worth in our society.
Anyway, let’s dive in.
1. I have to be able to enjoy living there
I have lived in every property that I have invested in. By doing so, I have been able to qualify for owner-occupied mortgages with lower interest rates and lower down payment requirements than I would have been able to get if I did not live in the property prior to renting it out. It’s outside of my area of expertise to get into the weeds of explaining different mortgage products out there, but your preferred mortgage professional would be happy to dig into this with you. If you don’t have a preferred mortgage partner yet and would like a recommendation, reach out to me and I’m happy to help connect you with one of mine.
Since I know that I’ll be spending a good chunk of time in any home that I choose to buy, I want to make sure that I’ll enjoy my time there. The layout/size of the house is important to me because of this, along with its condition and location. I personally enjoy buying a home that is already in great condition, with a few opportunities to make it cosmetically even better (maybe an outdated kitchen or bathroom, for example). This brings us to my second rule:
2. The home needs to have opportunities for “low-hanging fruit” improvements
Look, I’m not a general contractor and I’ve come to learn (the hard way) that I’m also not the most handy-person when it comes to home improvement projects. Because of this, I’ve generally stayed away from the heavy-fixer, handyman special homes that hit the market. However, that doesn’t mean that I want to buy something fully move-in ready either. Those “picture perfect” homes typically are way more competitive (since anybody who sees it falls in love with it) and these homes typically sell at the top of the market, and sometimes even higher than top of market.
By looking for a home that has some cosmetic deferred maintenance, I give myself an opportunity to “force appreciation” while I live there by tackling a few of these projects. My first house, for example, had an outdated bathroom on the main level – I was able to save up and hire a contractor to update it for me. This investment cost me a few grand, but immediately made my home more desirable down the road and positioned it to either sell for more money or to be able to rent it out for more money, which brings us to my third rule:
3. I always give myself multiple exit strategies
The market is unpredictable and I would have missed some truly amazing opportunities if I had tried to “time the market”. Instead, I opt to dive-in when my finances allow while making sure to give myself multiple exit strategies. What do I mean by this?
When I’m evaluating a property, it boils down to this crucial question: can I rent the home in today’s market for at least as much as the total monthly expenses associated with owning the property? This includes the mortgage payment (principal & interest), taxes & insurance, as well as an estimate for annual maintenance and expenses broken out into 12 equal monthly payments. For me, knowing I have this option in my back pocket is critical in case I find myself in a position where I want, or need, to move during a down-market where I would potentially lose money by selling my home. Speaking of hedging against risk.. We’ve made it to my fourth and final rule for today:
4. I maintain an emergency fund for each property
Everyone’s risk tolerance for how much of an emergency fund to maintain is going to be a little different. For me, I tend to fall more on the risk-averse side of this spectrum, and holding myself accountable to this rule ensures I will likely never become the owner of a large portfolio of rental properties, but it also stacks the deck in my favor for surviving the twists and turns that life throws at me, allowing me to hold on to my investments long enough to benefit from them. I watched worst-case scenarios play out in Florida back in 2008 that devastated so many people’s financial futures and that had a lasting influence on me. When figuring out the right balance for you, I highly recommend talking with a certified financial planner or advisor that you trust.
These rules are not all-encompassing, but they have served me well so far in my personal real estate journey. Thanks for reading, reach out and let me know some of your “rules of thumb” that you use to help you make real estate investment decisions!
Kyle Gordon
Broker | OR
He/Him
My career north star is to help you achieve favorable results for yourself in your real estate journey - whatever that may look like for you. Through the lens of experienced guidance and negotiation expertise, I have had the privilege of partnering with friends and clients here in Portland to achieve their real estate buying and selling goals since 2020...
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- T: 971-354-6475
- kyle@livingroomre.com
