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Hi Thomas, My daughter and I manage long term rentals in the Phoenix market and I can say that in the past couple of years we are seeing a trend of people doing exactly what you are considering.

I would say consider a low-cost index fund for now. 

He does a lot of BRRRR, flip, and hold between Pittsburgh and West Virginia and will surely know the Pittsburgh markets you are considering.

There are likely at least subtle differences between those proposals.In terms of good and bad experiences, you won't find an insurance company that doesn't produce happy and unhappy customers.  

Quote from @Sateesh Kumar: Hello,I am considering buying a fourplex in the Oakland area.

However, if you ever want to replace that home, you'll have to move it off his lot.I would consider appraising the vacant land and trying to cut a deal that's fair.

Consider house hacking and short-term rentals for reduced living expenses.

Consider Dauphin Island, Alabama. 

Make sure to conduct thorough due diligence on the areas you're interested in, including neighborhood dynamics and the condition of the properties you're considering.