I think you could sell an Airbnb making that kind of income in the wine country for that price range easily.

There's always a level of risk but if you do you research and seek out reviews, 3rd party references, etc you can easily avoid scams for the most part. 

You can easily make 30,000 gross on a $250,000 property just by buying older properties in areas with high long-term rent return on a property has three main inputs.

You can easily gauge how accurate your phone numbers are based on how your cold call campaign performs.1.

. -- ALL this coming from the perspective of - as a homeowner in a job-dense area, I can easily get 30-50 single roommate inquiries in a month for a room in my house where price is $700/mo vs a 1 BR apt which might be $1400/mo before utilities.

You could house hack your way to 6 properties in that time pretty easily.

If they are professional, they can explain this quickly and easily.

You can easily get there with 6 paid off homes.

Unfortunately where we live we'd have to easily shell out 350k to find a home that we would be happy with and that wouldn't really feel like progress to me, just more burden.

Zillow is great but because they use a standard algorithm it can easily be off by 20-50k.