Re: boats
But he specifically said he wanted to fish out of the boat too, which to me would rule out a V8 direct or V-drive. You could not trim it up to get into fishing spots. Also you would be firing up a v8 every time you needed to just move the boat a few feet.
Stingray, Bayliner, Glastron, and I beleive 4 winns all have IO versions set up for fishing too.
In the stingray, there is a live well. There are convertible sections that allow a fishing seat to be used. There is also a trolling motor option which would allow you to fish a spot all day long without firing up the engine.
IOs are no v-drive nor direct drive. However, if propped correctly, and if you ad a foil or smart tabs, they can hold plane at wakeboard speeds, and still have a decent wake to learn on.
If after a couple years he is ready to move to the next level with wakeboarding, then get the v-drive. There is an equal chance he might move even more in the direction of fishing, versus wakeboarding or water sports.
Thus, the best compromise seems to me, IMHO, to be an IO fish ski set up.