I am making a basic assumption here. You are not rich.
Rich, for the purposes of this discussion is someone who was born or inherited wealth. Wealth being enough money that you pay more attention to your portfolio than your job. Wealth being you have more than 50Kilobucks in the bank, excluding your retirement savings RRSPs, and 401K type things.
For the damned - you are decided anyhow on a boat.
The decision comes down to a three way race. Rock, paper, Scissors, or plastic. Also known as Ferro, wood, metal, or plastic.
Fibreglass actually has very little to do with glass fibres these days, and everything to do with plastic, so it is labelled thus.
Metal boats come in aluminum, and steel. You will likely see more steel than Al. Steel rusts. Mild steel rusts lots. Paint is key. Rust can be painted over.
Ferro cement boats are basically the bones of a steel boat dressed up kinky in chicken-wire, and then covered in mud to keep the water out. Eventually the mud cracks when you run into something. If you are lucky it cracks a little and you have to add more mud before the chickens escape through the rusty wire. If you are unlucky, the whole thing cracks like an egg and you end up with an 4x10^3 gallon enema as you flee your boat as it dives like a frightened U boat.
Don't bother with fancy electronics. Electronics rot in salt. Even if you buy them and keep them in a pelican case, technology has a shelf life slightly better than wax coated old cheddar. Slightly. Even a GPS will eventually lose its mind, and be unable to understand the babble of the new GPS birds up there. Firmware only gets you so far. Then it becomes unfirmware. Sextants never lose their charm, just their alignment and the silvering on the mirrors.
Books are your friends, but if you read too many of them, you will get it into your head that preparation is key to going to sea. Preparation is important to surviving when you are at sea. But the key thing to going to sea is simply going. There are some incredibly prepared people out there who will never get to sea. In the end they are as sad as the people who are perpetually prepared for the apocalypse. Although the people preparing for the apocalypse probably never had to choose sea anchors.
Small is beautiful. So is ugly. So is cheap. You will have more fun on an ugly, cheap, small boat than you ever will on a large, pretty, expensive one. Unless you are rich and can afford both the large pretty expensive boat. But in this case, you probably need therapy to get over the alienation of being obscenely rich, and the nervousness that comes with the unwavering certainty that people like me resent you a lot.
Shop carefully for a boat. It is a lot like getting that legendary uber-cheap first class upgraded airline seat. If you are hasty, you will wind up spending years worth of your salary on the wrong boat - while some bastard two weeks later will find a prettier, bigger, and more seaworthy beast for less than you would pay for a nice canoe.
Be wary of boat engines that look grungy, or look old. Grungy engines are unloved, and probably abused. They will likely take it out on you when they get a chance. Or they will commit suicide. Old engines are likely very reliable, owing to their existence till now. But finding parts may be more difficult than reaching a software developer through a support helpdesk at Symantec.
Headroom can be important. Damage to the prefrontal cortex has been shown to be a high risk factor for homelessness and voting conservative. You will likely be close enough to being homeless as it is, living on a boat. The exception to this rule is the Contessa 26, especially if you are short.
Anchors are your friends. If people laugh at you because your anchors are so damn huge, and your bow is nearly awash because you have so much chain and rode in it - then you might have nearly enough ground tackle to sail where there is coral.
Anchors can take on many shapes and sizes. Not all of them are metal. Some of them look shockingly like all the stuff in your house. Some anchors pay you money every month. Others kiss you goodnight when you go to sleep. Some of them you can haul onto the boat, and others you have to let go.
Carrying an outboard motor on a bicycle is hard. But so is eating a hamburger on a bicycle while riding one-handed down railroad-tracks.
I have done one of the above. Guess which one?
Hard dinghies look more stable than inflatables. Yeah right. But they row nicely.
My name is LuckyTroll, and I am a boat owner.