Re: Outboard size?
What you are going to run into is something known as "hull speed." When you are using the relatively low horsepower motor on your 26 foot boat, it will be operating as a displacement hull. If you watch a non-planing boat from the side, you will notice that the hull movement through the water creates a wave near the bow and one near the stern, with a trough in the middle. That is the "wave" that you climb out of when you throttle the main engine(s) up to plane the boat. Since any motor that you are likely to use as a "kicker" won't have enough horsepower to get you through the wave onto a plane, you will hit a maximum speed (hull speed) based on the waterline length of your boat. A more precise explanation of this (Froude's Law) is that a displacement hull will go no faster than the wave length that it creates as it advances through the water.
The way to calculate the hull speed of your boat is to take the square root of the waterline length and multiply that by 1.34. So, if your boat is 26' overall, but has a waterline length of 22', your hull speed would be 6.3 knots, or about 7.2 miles per hour.
There are ways to calculate just how much horsepower it would take to push your boat to hull speed but the process is somewhat complicated. Having had small motors on displacement hulls about the length of your boat, I would go with the 15 - 18hp range. I don't think you will need 18hp to get to hull speed but, a motor of that size should allow you to throttle back a bit for economy and less wear & tear.
PS: Remember that the speed of your boat is not only relative to the speed over the bottom but also to the water through which it is moving. In the example of having to move against fast moving water, if your boat has a hull speed of 6.3 knots and the water flow is 8 knots on your bow, you are going to make -1.7 knots over the bottom. To the degree that the motor you are using is unable to plane the boat, more horsepower isn't going to change that.