You have a unique combination of experience which can give a different perspective on real estate.

From a management and maintenance perspective, it seems like it would be more straightforward to handle four tenants at a single property as opposed to four separate properties.My primary question is:As I do research, I may find a handful or as few as one available property in a particular city.

It has to make sense from a business perspective & long term goals. 

I really appreciate your perspectives and will discuss further with my wife. 

I'm actually in the exact same boat as I'm looking at 5+ units in the Bay Area and still in the early stages.Regarding it being too simple - I think this perspective is a great one on the forced appreciation model within a seller's market: Trust that there are others who are trying to do exactly what you are, and that gets factored into people bidding up the purchase price and the compressed cap rates.

The STRs require much more time from a property management perspective, but also have higher returns.

If this is the case, from a building perspective, what are the cons of buying this property?

I believe there to be much better markets out there from a tax, legal, appreciation & cash flow perspective. 

Better off waiting tables one shift a month than spending 20% down to buy oneself a sub minimum wage job.

I've been looking for some perspective and I really appreciate yours.