Re: would boats be faster if outboards had gears+transmission?
If you could make one of the right size and strength for boat, something like a cvt (continuously variable transmission may be able to get high revs and thus lots of power to the prop at low speeds and that high resistance speed right before planing. Once on plane, the resistance is lower than when you're pushing water, so the cvt could slide down to the high output speed end and give a boosted top end. It's essentially a transmission with infinite ratios that when done correctly provides the right amount of torque and power when needed and speed when desired.
Also, since the basic premise of the transmission is a belt turning a cone, it can "slide" between ratios without having to engage a clutch and stop power transmission to the prop while shifting. It also offers theoretically infinite ratios between the low (maybe 5:1) and high (possibly 1:1 or 1.5:1, depending on horsepower) ends of the range. The only problem I can see with this is longevity, belts aren't the strongest and cvt's are usually used on atv's and compact cars with little 4-bangers. On a big v8 with 500 hp, you'd either slip the belt or burn it up in a hurry. Another issue is fitting the machinery in a stern drive.
But if you could make it work, it'd be the equivalent of clutching during a drag race: keep the rpm's the same throughout the launch (usually where the best torque is) while gradually letting out the clutch to increase speed.