Customer service is A+.

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.

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.

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.  

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.

Another factor to consider is the part of town your property is in and if you would have more issues with tenants due to issues with shared space.