I've always instinctively crossed a wake well back of a boat I am coming up on from behind, and maybe a bit closer when coming into each other...all depending on how wide I can go with avoiding other boats, shallows, buoys etc. My boat is a 26' Hewes Alaskan, so not little, not big, plenty of power with twins.
This Fall I was on a charter with a young captain in the Charleston, SC flats. 17' bay boat, wide and flat with shallow draft, 70hp Yahama. We passed a lot of boats in the channel going to and from the flats, many big bluewater boats with a big wake. He would get right up behind them, then quickly pass over their wake on their starboard side....seemed to go pretty smooth. Coming into each other was a different technique for him, he would catch the coming wake maybe 50-75 yards after he passed the other boat, go sideways (yeah, I know, seems weird...) and slow quickly and take the wake on his port side and just let it roll under him. I asked him, and he said an "old guy" showed him both techniques and they did seem to work great on his boat. I am particularly wondering about passing a boat by coming up on its stern maybe only 30 feet or so back... what do you think and what works for you?