A Tale of Two Cities – and Clients

  

As someone who’s grown up in the Portland suburbs, and moved away for college + my 20s, 30s and 40’s; then having returned in my 50s, I feel I’ve got somewhat of a unique perspective on Portland.

The time away has given me the distance and the opportunity to appreciate all the things inherently Portland; the changes to the city that have happened over the decades – the growth, the people, the nature.

Like others who have lived in other major cities, and returned to Portland – very much on purpose, and carefully chosen, I might add — I can dispassionately compare and contrast. between, say, San Francisco, LA, Seattle — even New York. Housing prices, quality of life, density, crime and homelessness. Walkability, traffic, parks/arts/recreation. Portland’s doing great, and there’s no where else I would rather live.

Let’s call them David and Richard. They are friends of friends and re-lo clients from Texas: dear and wonderful people with incredible lives in progress, careers full swing and having lived in the Houston suburbs, then Dallas for years. They’re travelers, with sophisticated and varied tastes, who, after some time have decided that Texas wouldn’t be home forever.

Having had the shared friends who lived in the Houston suburbs and Austin both that I’ve mentioned, and witnessed their joyous part time move to Portland in 2023, their interest in something similar was piqued. They came for a visit in 2024 and we did a high level Portland tour – the neighborhoods, the quadrants, the outlying areas. They got a taste for the personality and what could be available to them here: the homes, the job market, etc. They liked it. A lot.

But life and its demands played the timing a little differently than they first imagined, and plans for the move were put on hold. They wanted to make the leap from being Texans to being Oregonians but it was going to be a slower roll. All the while though, dedicating free time to research, home listings and check in calls as Portland has gone through it’s last little bit of celebrity – and all the fuss – real or advertised. David and Richard checked in re protests, ICE, etc – was Portland really a wasteland now? On fire? A warzone? I kept them up to speed on what the reality was and we exchanged favorite listings.

Fast forward to this past month: November of 2025 when they decided that they wanted to check in on their dream destination in the gloomiest, wettest, real-est time of the year. They were going to take a trip – six days where they would stay downtown and do some investigation. News reports had warned of all kinds of stains on the fabric of our Rose City, and they wanted to see what percentage of that was true.

We met at the incredible Yaowarat for dinner on their last night, to hear the full story straight from their mouths. They had been all over Portland – Downtown to Sellwood; Multnomah Village, out to Bethany – they had been in Old Town and the Park Blocks after dark, they had walked through Washington Park and it’s drippy beauty. Their report was delivered authentically, and not without critique, but the overall take was “what exactly is the problem??”

They saw homeless. They saw drug use, they saw resources being applied to said, and a change since their last visit – for the better. They saw and were met with friendliness and inclusion; smiles and positivity, a vibrant, alive and bright downtown area, and exciting neighborhoods with folks of all kinds and colors and backgrounds getting along and making a life. They saw arts and entertainment, they saw beautiful homes from Lake Oswego to Laurelhurst, and I’ll tell you what – I’ve never seen a couple happier or more excited, even, as I said, in the midst of a very mushy and dark late November week.

So this is my tale of two cities – two clients, and although a small sample size, I think it represents the overall sentiment that we share here in Portland, and gives an idea, for those wondering what it’s like to live in Portland, or what it might be like to move to Portland. And if you want more detail or a personal experience of your own, be sure to let me know.