I bought my house at 27 years of age and my mortgage is ~$1000 per month. That was by working remotely, mostly for Bay Area companies but also others, from a low-cost town in Washington state. I'm sure that it's easier to find new and better jobs when you have a physical presence near a major software hub. The extra difficulty in job-hunting has not outweighed the benefits of affordable housing so far. Living off savings between jobs is easier when you spend under $2000/month on necessities.
I'm investigating similar options at the moment, but having a spouse who isn't remote complicates things a bit. Even so the idea that changing cities (countries, even) wouldn't necessarily mean changing jobs is a relief.
