Supplement this far simpler entity approach by ensuring you have appropriate types and levels of insurance, you operate your business in a manner in which your conduct is not considered an exclusion in your policy, you work with licensed and insured vendors, you execute contracts with indemnification clauses with these same vendors/ require additional insured status &  maintain appropriate licensing and permits.

Quote from @Mike Grudzien: Two thoughts:1) stay in your STR for a day or two and you'll discover things it needs or that would be nice to add2) use several touch-points to communicate with Travelers/Guests.

Add thoughtful touches like a Keurig or French press, USB chargers, and local travel guides.

We want to be traveling and sailing throughout the year, not just when a job allows me to use my 10 days of vacation.

I suppose I could combine the two ideas and live in a basement while renting out a 2 bedroom home to a traveling agency. 

Addendums can be added to a contract (in most cases), which modify the original contract, when legally executed (per the original contact terms). 

Temporary work travelers etc.

These are also the banks that are more commonly relationship lenders and will allow your originations to out pace your balance sheet if you are consistently able to execute on the projects they fund for you.

@Jon Latorre I'm traveling to CR next week.

You have to really understand your funnel and market segment as well as execute extremely well for this to work.