I ski 3-5x a week behind a direct drive ski boat. I love it. And I still ski a bunch behind an 18’ Glastron with an outboard. the typical mid-size outboard boat weighs about 600 lb less than an I/O. Less weight, less wake, better hole shot AND more interior room as the motor isn’t pushed into the boat. 7-8 people in the boat on an evening cruise and everyone is happy. Like any boat, when skiing, two in the boat is best.
Getting a ski on and into the water from the boat is not as easy, but if you can ski off a dock, no problem. We’ve got a carbed 150hp V6 2-stroke OMC and it’s quiet, trouble free and requires no winterization. None. We added hydraulic steering which I’d recommend on a bigger outboard - much less muscle required to drive.
It is not a sexy looking boat, but if you’re never skiing a course it will track just fine, pull you out of the water just fine (we’ve had 8 skiers pulled up behind the lowly Glastron) and with line shortened to 22 or 28 off, I get into a reasonable part of the wake that I can rip right through. Oh and if you care, it’s waaaay faster than any DD tournament boat you’re going to find. And it will trailer behind a minivan.
Wake pic below has all skiers at 15’ off. Wake flattens a bit closer to boat, but very skiable.