Should effort be placed in a baseline business plan to determine the best option to start in for this field?

If you ever need assistance or guidance with financing options for your project, feel free to reach out.

One option I'm considering is adding the equivalent of a camelback, or second story over one side of the home, adding ~900-1000sqft and 2 or 3 bedrooms. 

Sounds like you have some interesting options, and good reasons for both! 

On VRBO, when we set up the listing, they didn't have a "loft" option, so I think it's considered office space which led to some confusion or set up as a second living area.

It just obviously won't be market specific.On a personal rezoning I did for a house hack new-construction triplex, I was asked numerous questions about how many bushes and trees I was going to plant.

I want to know the options and you are certainly gave  me good info. 

I'm currently in the option period with it ending on Monday so I need to make an educated decision by then.

Also Solo 401k could be a better option for you if you're self employed with no FT W2 employees.   

Have you considered the idea of house hacking as an option?