Those long jaunts were temporary so we could sail different coastlines for seasons or long stints. I could see doing the long distance temporarily again, if the sailing grounds were worth the trip. Full time, if you paid a yard to maintain the boat, it makes sense to travel. Like a second home you travel to, most people don't live near their second home.
But the 5 minute walk is the best by far because we're in a great sailing ground. It might not be too much fun if you walked 5 minutes to the boat, but needed to motor 2 hours or more to open water. In that case, I'd rather drive 10-15 minutes and have the boat waiting in a good sailing ground. Sailing grounds vary tremendously.