You will likely be negative cash flow unless you can increase revenue somehow. 

In those instances you can purchase the new property in 'cash' position and do not have to get an additional mortgage. 

I don't track the STR market closely on Big Island, but I have had clients look on that island and think you should find something there that cash flows pretty well. 

Just play close to the vest, please use common sense, no one loves your $$ more than you, be smart and always pay attention and ask questions tol you are satisfied if something does not make sense!!!

My goals are to just get started with at least positive cash flow.

My hope is to begin the investing journey with using as much as our own cash as possible.

Partner would bring $500K cash and thus own 50%.1.

Everyone gets the same played out cookie cutter guru garbage as everyone else.

The difference only comes into play with rentals or other holding investments. 2.

Asset class, price range, neighborhood type, cash flow/appreciation, whether you want a rental portfolio or get into rehabs...It's easier to start from the goals and work backwards.