I once had a delivery job that allowed me to drive through various parts of the state and the sense of exploration allowed me to alleviate some of the pain in my chest, however the feeling of inadequacy of not being able to find a job that could fully support an independent life were always there.

My response, and the response of all owners should be, "well, the best thing you could is do an internet search about the statistics here".  

When I get my real estate license, do I have to be with a broker or can I be independent?

Whether you use desktop or online, in my opinion, depends on the amount of collaboration you desire with others and if you prefer to be location independent (the online version can be accessed from anywhere & shared with a bookkeeper or CPA).  

My guy is landscaping company by weekday and independent contractor weeknights and weekends. 

They both have great schools and positive crime statistics. 

Never known what its like to be independent.

Unfortunately if they are independent you can't use that strategy. 

I am wondering if anyone here has been involved with Independent Senior living type of business and can share their thoughts/experiences (e.g. builders, investors on REIT's, people living in these facilities, etc). 

Hi Skylar - I'm not familiar with pricing in your region, but contacting a trustworthy Independent Insurance Agent in your area will help a lot.