(Courtesy of Dave Kinzer)
Powerboats differ from sailboats in that sailors use their boats simply to sail, but most powerboaters use their boats to do something else such as waterskiing and fishing , so the ``best'' first boat could differ greatly from person to person. Therefore, you should feel free to disregard any piece of advice in this section as it might not be applicable to your specific situation.
To begin with, you should look at the types of boats that are popular in your area for the activities you plan. Boats that do not work well in a region usually don't sell in great number, so you can learn by other people's mistakes here. Talk to owners to find what they like and dislike in their boats. This will help you get an eye for details that will count after time.
Second, think small. A smaller boat is easier to muscle around, and and less likely to be damaged severely during the learning process. It will cost less, and if for some reason you end up not liking the actuality of ownership (think of burning 100 dollar bills for fun,) the loss will be minimized. I'll contradict myself here and say get one size bigger than the smallest suitable boat. This will give you some more time before outgrowing it. Keep in mind your vehicle's capacity to trailer it.
Third, buy used. There is a lot of argument on this point, and I respect the other point of view, so I will present both sides. With a new boat you have a warranty to protect you in the event something goes wrong. If you have a good dealer, any problems will be resolved promptly, and you will be back on the water with little or no out-of- pocket expense. If you have a bad dealer, your boat will sit at the back of the queue for the boating season while the paying customers get their boats fixed (I know someone this happened to.) Buying a boat a few years old will save you a bunch of money that can be used for repairs, if needed. Have a mechanic check out the boat before you buy to minimize the chance of having to use that money. A used boat will probably have some equipment already installed (like radios, depth or fishfinders, etc.) that you would have to buy for a new boat. Finally, when you scrape your boat while learning near a dock, you won't have to wince as hard.
I have managed to get this far without giving any specifics on what to buy. My OPINION follows, with some thoughts as to why I believe them. Start with a boat about 3 years old. A newer boat will depreciate more, an older one may have problems that it takes an expert to find. This is also about the time the first owner has discovered he either doesn't like this enough, or it is time to get a 3 foot longer boat. A good length would be 16-18 feet. This is big enough to comfortably have some friends on, yet small enough that you do not need a special tow vehicle. I recommend a single outboard or I/O (stern) drive. Two engines aren't needed for this length, and you don't want the expense to begin with. There are arguments all over the place on I/O vs. outboard; I suggest you go with what is popular in your area, for parts and service availability. The important thing is that they handle the same in low speed maneuvering. Inboards, V-Drives and jet-drives do some funny things (which are predictable, once you know them) that are better left for learning later. If you are planning on skiing, get enough horsepower. For an I/O drive, this means a V6. Your towing vehicle capacity could decide the I/O vs. outboard question. The outboard will need slightly less horsepower, and will be considerably lighter.
Last, but not least, sign up for a boating safety course. There are enough dimwits out there already, you don't need to make the situation worse. It is not enough to say that you won't do anything stupid since you don't know what the stupid things are yet. (dk1)