@rogger I relate to this SO MUCH. I absolutely wish we would have bought a larger "starter" home because, surprise! It's our forever home now. I thought we would start our family here, but then size up...
We're in an average cost-of-living small city but there is a massive housing shortage. Sizing up would require us to move 45 minutes outside of the city, at least. Our location is prime (walking distance to grocery store, library on the next block, ample parks, 15 minute commute...) and I refuse to give it up.
I go back and forth between grounding myself in reality -- most families around the world do NOT have 1000+ square feet -- and feeling totally suffocated by our very small (sub-800sq foot) home. Not to mention I'm pretty sure our kid will be very tall as a teenager. I can't even think about that yet.
Related: this is why Millenials don't host. I'd love to host a holiday get-together or friends for the weekend. But...guest bedroom? Guest BATHROOM? A large enough dining table for a crowd? I wish...