I'm taking the 104 to Peru for sure, the wind can be very light.
Tofino is often very light as well, and you need to make it out through the whitewater so the bigger the better.
I think for getting into wavesailing a bigger board will make it a far easier learning curve. For us non pros the goal is to catch a wave and make some turns, not to have critical into the pocket vertical turns, a 99 l will do that just fine, and with good technique will do exactly what you want.
I never use a wave board at Squamish, those extra fins are doing nothing but slow the board down. A freestyle board is the way to go as you know. Or a slalom/ freeride board if you like to go faster, and not try any tricks.