I think the answer is, "who is going to look after the boat in between trips?" I would have no trouble leaving a boat in my marina for an extended time period,* because the marina staff watches after boats and takes action to protect them. And during storms the other boaters pitch in and help out with securing boats and letting owners know of problems. There are other marinas I would not trust to look after my boat in my absence.What insight I'd like to garner from this topic is what those of you who are far away from your boat actually have in place to attend to things that can, and unexpectedly do, go off the rails.
For example, one day I got a short video clip of my boat from the manager, he wanted to know why my bilge pump was running so long and should he do something about it. I told him not to worry, it was my water cooled refrigeration.
*Well, I would leave my boat there for long periods of time if it wasn't for that ice issue.