Here's some advice to the younger boaters who currently don't own a boat, from an old man that has owned 17 boats in his 71-year lifetime.
First and foremost, you don't need to buy a new boat. In many respects it will depreciate as fast as a car, and at about the same rate of depreciation. Buy used - it's the best way to go, especially if you've never owned a boat.
Next, don't buy a boat from a friend unless you no longer want him or her as friends. Friends always seem to believe they can get top dollar for a boat they either can no longer afford, or no longer want.
Think smaller. Everyone would love to have a boat big enough to sail around the globe and live comfortably on. Odds are that you will NOT sail circumnavigate the globe - even if you're young. Try your hand a day sailing, maybe some overnights to a not too distant cove or creek and enjoy the waters close to home. I know lots of folks that have trailerable sailboats that they store in the driveway or behind the house when they're working, then haul it to a new place every weekend and explore new vistas that are just a short drive from home. Others that live in apartments store their boats on marina parking lots, thereby eliminating the task of putting the mast and rigging in place every time they want to go sailing. Saves them lots of time and money.
If and when you decide that you wish to go bigger, take your time and do some research before taking the plunge and buying something that must remain at a marina because it's too large to transport. Do some internet shopping, but also drive to all the nearby marinas and talk with the dockmaster to find out if there is a make and model of the boat you are primarily interested in available at that location. More often than not you will find it using this method, or the dockmaster can point you in the direction of where that boat may be located.
Derelict boats can be found in nearly every marina, large or small. These boats are not always junkers that are ready for the scrap heap. Many have been abandoned simply because the owner has passed away and the marina has a storage lean on the boat in hopes of regaining some of their losses for slip rent or dry storage. I've seen some 27-Catalinas in excellent condition go for as little as $4,000 and more recently saw a 30-Catalina-T go for under $10,000, which was the repair bill when the owner said he was tired of boating and walked away.
For the most part, the youngsters, folks under age 30, that I've encountered seem to want something that goes fast, you only need to insert a key and fill it with gas and you can travel 100 miles in less than 3 hours. I was that way until I was about 60 years old. Now, I'm not in a hurry to get anywhere - even when driving the van. Guess that's among the many reasons sailing caught my interest.
Hope this helps some of you youngsters that are pondering what direction to go,