Alright, let me walk you through this little project I did, comparing Portland and San Francisco. It wasn’t anything super formal, just me trying to figure some things out, make a sort of prediction for myself, really.

It started pretty simply. I was thinking about maybe relocating or just spending more time on the West Coast, and these two cities kept popping up. Portland, San Francisco. Both have their reputations, right? So I thought, let’s try and nail down some actual differences, maybe predict what a move or an extended stay might really feel like, cost-wise and vibe-wise.
Getting Started – Just Gathering Thoughts
First thing I did was just brainstorm. What did I want to compare? The big things came to mind quick:
- Cost of living (housing, food, getting around)
- Job vibes (what kind of work is big there?)
- Getting between them (flights, driving – how much hassle, how much cash?)
- The general ‘feel’ (harder to measure, but important!)
Didn’t have a fancy plan. Just started grabbing bits of info here and there. Felt like making a big scrapbook at first.
Digging into the Numbers (and the Mess)
Okay, this part took some legwork. I started hitting up websites. Looked at apartment rental sites for average prices in different neighborhoods. Checked out grocery store prices online where I could. Looked at flight costs over a few weeks, same for estimated driving times and gas costs. Man, the data was all over the place. Especially housing. One site says one thing, another says something totally different. You really gotta take averages and be skeptical.
I wasn’t using any fancy tools. Honestly, most of it ended up in a simple spreadsheet. I made columns for Portland, columns for SF. Rows for rent (1 bed, 2 bed), groceries (a basic basket I made up), gas, maybe a sample flight cost, stuff like that. I also poked around job boards, just getting a feel for the dominant industries in each place. SF is obviously heavy on tech, Portland felt a bit more varied, maybe more creative and manufacturing alongside some tech.

For the ‘vibe’ thing, that was tougher. I read blogs, forums, watched some videos people posted. Tried to get a sense of the daily life, the pace. This part is super subjective, obviously, but I noted down common themes people mentioned.
Making Sense of It – The “Prediction” Part
So after staring at my messy spreadsheet and notes for a while, patterns started to show up. No huge surprises, honestly, but seeing the numbers side-by-side made it concrete.
My main takeaway, my “prediction” if you will, was this: Moving to SF from somewhere cheaper, you’re gonna feel that price jump immediately and significantly, especially rent. It’s no joke. Portland felt way more manageable, though not exactly ‘cheap’ cheap anymore. The prediction on travel was that flying between them is pretty quick and often not crazy expensive if you book ahead, while driving is a long haul but doable for a big move.
Job-wise, the prediction was kinda obvious: SF offers potentially higher salaries, especially in tech, but that gets eaten up fast by the cost of living. Portland seemed like a place where your money might go further, even if the top-end salaries aren’t as high. The ‘vibe prediction’ was that SF would feel faster, more career-focused, while Portland would be more laid-back, maybe a bit more focused on lifestyle outside of work.
Wrapping Up – What I Learned
Doing this wasn’t about building some complex predictive model. It was about grounding my own thoughts and expectations in some real-world numbers and observations. It helped me get a clearer picture than just reading articles saying “SF is expensive” or “Portland is weird”.

It definitely made me appreciate how much variation there is even within cities (different neighborhoods have wildly different costs and feels). And it reminded me that finding good, consistent data for this stuff is harder than you’d think. Lots of noise out there.
So yeah, that was my little Portland-San Francisco prediction exercise. Just me, a spreadsheet, and a bunch of browser tabs. But hey, it gave me a much better handle on things.