When looking to buy a boat, you have three choices
Used in wonderful condition
Used in poor condition
At face value, Brand New is the most expensive, Used in wonderful condition is pricey but great value, and Used in poor condition is the cheapest upfront. But what does it mean for you?
Buying Brand New has the advantage of knowing that everything on the boat is fresh from the factory and should work flawlessly. This also means that if there are design flaws, you will be the one to find them. Most reputable boat companies will pay to correct design flaws in your vessel, so you do have some insurance there. The downside comes in the way of drastic depreciation. A $250,000 yacht will not be worth that in a few years, and if you ever go to sell it, you will realize that depreciation took most of the boats value.
Buying in wonderful condition is where you buy a boat that was bought Brand New and meticulously maintained for years. All the while, problems have been discovered and then fixed along the way; delivering to you a like new yacht with all the kinks worked out! This can be the best way to buy a boat if you can find the exact boat you are looking for.
Buying in poor condition is a bit of a risk. You are essentially buying a deck and hull, and outfitting the rest from there. Cost wise, this tends to be the cheapest upfront, but the costs of outfitting a boat can add up considerably. The advantage is this can be done in stages allowing you to save up between stages. This way, you are able to have a place to live in (or camp in) while you work your way towards perfection.
They say boats cost! They cost money and time, if you save on money, you will pay more in time!
From the choices above, it may seem that buying "Used in wonderful condition" is the best choice, as the price is greatly reduced over new, and it won't cost you any time to get the yacht ready to sail. This is true, but it is also very hard to find the boat that is exactly how you want it.
If you look at any sailboat, you will see "Owner Customizations". Some people want radar, chart plotter, auto pilot, and a wine cooler; while others want laminated sails and light weight synthetic rigging. What you want on a boat is not always what others want on their boat. This means that no matter what boat you buy, you are going to sink more money into it to make it "Your Boat"
This is where buying "Used in poor condition" shines. The boat doesn't cost much and is a blank canvas! When you buy a quality boat that is in need of a rebuild, you are buying a sturdy platform to build your dream boat on. You are in control of deciding what goes where and you are able to spend your money on the items that you value as necessary on board your boat.
This method will cost you a lot of time if you do the work yourself, but I think it's worth it in the end. How much of a project you want is completely up to you. You can get a wooden boat from "Boneyard Boats" for free, or a sunken boat that has been resurfaced for nearly free. These are the cheapest initially, but the total cost of these projects will quickly overshadow the supposed deal.
The next option is to buy an old boat that has a good interior, deck, hull, rudder, and spars; and take it from there. These tend to be boats that were loved and used for many years, and are in need of a re-fit. They tend to have a bad engine, blown out sails, aged rigging, and minimal electronics. These are where the true bargains are hiding! You don't have to pay the previous owner for "his favorite" chart plotter and then replacing it with "your favorite" chart plotter. Instead, you can pick and choose what and where you want to mount your electronic accessories.
The other advantage with boats that are structurally sound is you get to pick and choose what sails and rigging you desire. If you prefer tri radial sails over crosscut sails, or full battens over partial battens, you don't have to live with the previous owners decision! You can choose exactly what sails you want and what size for them to be! Some people prefer to have a smaller high aspect jib while others prefer a monstrous 180% genoa, the choice is yours!
As far as rigging goes, you are free to select the color scheme that makes sense for you! If you want all the downhauls to be the same color, or if you want each line to be a different color, this is your chance to decide on color and feel in your hands. Boats like these take some time to complete, but the owners tend to be very pleased with the end result.
It can be hard to find your perfect yacht when shopping around. The eyes will love a brand new boat much more than your wallet will. The used market might seem daunting to sift through. Keep searching with an open mind, and consider looking at the ones the eyes might not fall in love with right away, but have the potential to make your dreams come true!