>>2038333The only way for it to be possible would be to get a job online/work from "home"
But to do that you have to stay in port. The Puget sound thru Salish sea would work for something like this, as there is unlimited free anchorage spots and cheap moorage through the area with good wifi and phone service.
Im saying this from personal experience from a fella I know. In the harbor I live in there is a fella who lives on a 27' sailboat and makes a living flipping free abandoned boats (to my knowledge as he tried to sell me a boat (was a really damn good price too)). The man anchors in my town for a max of 28 days then move to the next harbor over or up to the San Juan Islands. He uses a dinghy to get to the dock and uses the public bus to get to the store and stuff. The guy also has a dog named Quagmire which I think is pretty impressive to live on a boat with a dog. I've seen him take the dog into the bus too by putting him in a backpack. I personally wouldn't want to live this life though, the guy looks rough and kinda seems to have some mental problems. He freaked me out the first time my friends and I met him which was when his dog barked at us.