Over my 40 plus years of boating, I have had outboards, inboards and that god-awful hybrid the inboard-outboard. Currntly have a 26' Excel with VP I/O and a 16' center console with a 50 HP Honda outboard. Used to be inboards did outlast outboards by a large margin, but I also believe that has changed in the last three years or so.
Straight inboards were pretty reliable and used to be easy for the common guy to work on as they were essentially automotive based designs with a few unique marine parts. However, they took up a lot of room inside the hull and manufacturers seemed to delight in placing them in areas that were difficult to get into for work and several designs even required cutting out decks and cabin doors to replace old motors with new. The inhererent fixed geometry of the driveline also meant that you had to be really careful of paying attention to your water depth. The constant intake of sea water from the drive shaft packing gland also meant constantly wet bilges, at least before the introduction of dripless fittings.
Stern drives had several advantages over straight inboards and outboards in that the power trim and tilt meant the boat was easier to trim fore-and-aft, faster hole shots and manufacturers almost always had the engines located under large access hatches that made maintenance and replacement a lot easier. The variable drive line geometry also meant that if you suddenly found yourself in skinny water (hey, it has happenend to us all)you could tilt up the lower unit and usually power your way out into deeper water. However, the numerous bellows, seals, gaskets and all that aluminum hanging down in the salt water made maintenance an almost daily chore and some of those clamps inside the transom shield required a person to have two elbows on the same arm and fingers the size of a two year old to replace. I/O's did have pretty good longevity for the engine part though and replacement parts were fairy easy to come by and comparatively inexpensive as the main engine components such as pistons, rods, intake manifolds, etc could be bought at local auto parts stores. With half the drive components outside the hull, these drive systems took up less space that a straight inboard.
Older two stroke outboards were loud, stinky, tempramental and they were major pollutors of both air and water. They sucked fuel at a prodiguous rate for their horsepower too. However, they took up no room inside the hull, were readily accessible for both maintenance and replacement, had variable geometry with the power trim and tilt systems and were fairly easy for the average owner to work on. I have a friend with a Yellowfin center console powered by two Mercury 250 four strokes and in the three years we have been fishing together, these have seemed to be a nearly ideal propulsion system. The one time something went wrong with one of them, the engine electronics placed the motor in a "limp home" mode and we made it back in from 20 miles offshore with no problems - turned out to be a bad sensor and the total bill came to $126 including labor. These newer outboards are really impressive with their lower noise, cleaner emissions and vastly improved reliability.
I think the current generation of high horsepower, four-stroke outboards is already drastically changing the boating business model. For now those changes are sort of focused on the market segment of vessels 32 feet and under, but almost monthly I see new models larger than that powered by outboards. While the larger boats meant for offshore fishing have been the trend setters, it is only a matter of time before we see the so-called "express cruiser" and "pleasure yacht" segments also convert over.
My only reservation about large displacement outboards on bigger boats is in the area of engine block corrosion. I don't believe I have seen an outboard in the 250 to 300 HP range that has a closed engine cooling system. If these engines are going to be used on larger boats that get more time in the water, then that appears to me to be an issue.
If I had the choice of propulsion on a new vessel, I believe I would opt for the outboards every time.