To win this game you need to figure out what you should sell/give away/throw away, what needs to be stored with family (hopefully very little), and what will be needed and can fit on the boat. It is a game we have actually been playing for a while. It started when I first drove from Colorado to Florida to move onto the boat. It continued as we planned and held our estate sale. And it continues today as we try to empty the house of the last of our stuff and prepare for the final move onto the boat.
To make the game a bit more challenging, I added an additional rule to our version of the game. Everything we plan to take to the boat needs to fit in the Prius that we intend to take on the drive back to to the boat. That includes the two human and two canine passengers. I figure this way we definitely won't arrive at the boat with more stuff than will fit on her. After all, I've been living on it for the better part of a year so it already has many of the necessities for day-to-day life.
This is a challenging game. You know there are some things you will need, there are other things you think you would like to have, some you can do without, and there are others that fall under the "what was I thinking when I bought that" category (anyone that ever owned a bread maker want to chime in here?). These needs and wants are stacked against the very limited space available to store things on a boat. Because, lets admit it, if you are storing your canned goods underneath your sofa, you just don't have an excess of storage space.
Some things are easy...while that clothes dryer might be nice, it definitely won't fit and I can't power it from the inverter (so, it left to a new owner just a few hours ago). The ski rack, while it might fit somewhere on the boat, isn't exactly useful on a sailboat. But what about our bicycles? They are hybrid bikes (part road and part mountain bike) and have quick release hubs so they can partially collapse for storage...but not as much as a folding bike would. They are likely more comfortable to ride than the folding bikes...but would definitely be more difficult to dinghy to shore.
Some clothes we definitely want to take. Swimsuits, wet-suits, t-shirts, and shorts generally make the cut...at least a few good ones. But do I need a dress suit? How about a nice sports coat...and where will I store it on the boat if I take it. I've never been much of a dress up kinda guy and Colorado is pretty casual, so I've only needed these things on maybe a dozen occasions my entire lifetime.
There have been a few things I've already lost this game on. When we had the estate sale, I sold a heat gun and had to buy one for the boat. Same with a car buffer and a few other tools. And with the colder temperatures that I wasn't expecting to be around in, some sweatshirts needed to be acquired in Virginia and Georgia as well. And there are other items that I already carted across the country that I have yet to use on the boat. Don't know if I will...but haven't thrown many of them away just yet.
In any case, we keep on playing the game. Pairing down the things we need in hopes that our choices keep us from getting rid of too many items that we will later have to reacquire. And just as bad, carrying stuff half way across the U.S. just to toss it in a few months on the East coast.