I've had a boat additction since my grandad gave my a small wood boat to play on a pond. First of all, the two happiest days of a boatowners life are: when he buys the boat..and, when he sells the boat.
Now, there are basically three types of "pleasure boats" (i'm sure i will get arguments) these three types refer to how the boat is powered:
Inboard - the engine sits inside the boat under the gunwales. The prop shaft goes thru the bottom of the boat. (my personal preferance)
Inboard/Outboard - the engine is still inside the boat but the drive mechanism (outdrive)
goes thru a hole in the transom (stern) of the boat to provide power.
Outboard - the engine and drive are one unit and all is mounted to the transom and sit outside the boat.
In/Outs and Inboards are modified auto engines. Outboards are a technology to themselves. Anyone with mechanical knowledge can do minor maintenance on Ins & In/Outs. With a manual and some guidance you can winterize yourself and save a ton of money.
If you're going to be skiing, wakeboarding etc. An inboard is your best bet. The power goes from the engine thru a two gear (forward/reverse) automatic transmission and produces much more thrust than the In/Outs. They have less moving parts than In/Outs and are generally more reliable and hold their value. The big three brands in Inboards are: Malibu, Correct Craft (Nautiques) and MasterCraft. I've owned several Correct Craft's over the yrs but now I own Malibu because of the quality of manufacturer. I'm sure the MasterCraft people will be all over this statement but, I've seen them all built so it's my personal preference. Also, go with a fuel injected boat with electronic ignition. It will give you much better service.
Remember a boat is like any other depreciating asset. The more you care for it the more you will get when you decide to upgrade of get out of the business.