Without some background as to debt levels, income/taxation level, asset type, investing strategy, their why etc it is similar to asking what is the best play in football for sure.   

Another place with similar location and Conditon sold for 173k with no second lot or 2 car garage and rent was only $1750.

With more than 40,000 in the Metroplex proper.People in other areas would be shocked if they saw our construction rates.I know some of the small communities around here that are similar to the following...10,000 population200 homes being built a month.400-1000 new apartments in development about to start construction.While that number of apartments might be needed within the next 3 years it might take to years to absorb them.It is the same in the high end areas.  

I would love to meet those who have similar interests whether new or seasoned investors. 

My wife and I have similar aspirations as @David Lemley. 

Has anyone else been in a similar situation?

Similar to @Rob Brown we own a duplex in Mission Beach (San Diego) one block from the ocean and 2 blocks north of Belmont Park. 

Your military work history can be included if what you do now is similar to what you did in the military. 

At what point does it make sense to open an LLC or similar for this business?

I suggested a 1031 exchange - as the parties would be ok with trading for a property of similar or higher value much closer to where the elderly friend resides.