Short-term rentals can be a great starting point, especially in markets with high tourism or business travel.

Travelers, Farmers, Steadily are some who allow this model.

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.

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

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'm sure y'all already knew that!

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

The asset may be fine, but the budgets are too small to actually execute.  

, it's still highly unlikely that an appraiser would have given value to this bathroom in any case, so we're not losing anything from an appraised value standpoint.Seller should be more than OK with it once you educate them on the fact that of all the offers they are evaluating, yours is the only one willing and able to execute a plan to close on-time, without delay, in spite of the flagrantly illegal and unpermitted bathroom.

Investment product marketers who claim to be GPs, GPs who claim “ownership”, insurance salesman who claim to be “financial advisors”, people who attended an executive training program claiming to have an MBA, what ever happened to honesty?