Step one: buy artwork from Hunter.
a) Hunter goes and visits his dad
Step two: head to one of Joe's vacation properties.
Step three: the meet takes place with no visitor logs.
Step four: Hunter pays the monthly rent to Joe.
aka the vigorish
Renting out your property is perfectly legal.
Renting a property, living there, perfectly legal.
Going on vacation, is perfectly legal.
Buying artwork, is perfectly legal.
Going to a beach in Delaware, is perfectly legal.
A son visiting his father, perfectly normal, perfectly legal.