Take it from someone in the Great Lakes state. There are TWO things in life you can never get rid of. Aids and Bayliners.
The first five are good to go. Cobalt, Chaparral are more flashy. Wellcraft and Four Winns aren't often as "pretty" but are very solidly made. Of your second list, Formula and Donzi are like Cobalt and Chaparral. Well, Donzi I think only makes cigarette style boats? Or did. Sea-Rays look nice when new, but my buddies fell apart fast.
Going to need a hell of a motor, and a strong pitch if you want to pull up skiers with a cuddy cabin type boat. That same pitch won't be good for longer trips either. As another poster noted, you're looking for a swiss army knife boat, and you're going to have to sacrifice something to get something else. Gotta prioritize that list better.
Have you looked at the prices of them bastads yet? Omfg. I bought a new Baja 18' bow rider in '93. Kept in the garage or under a hoist canopy year round, it never aged. Then I had to shrink wrap it and store it outside. 3 winters, and it was shot. I was going to buy a new one, but DAMN those prices! I ended up recarpeting and reupholstering the '93 Baja, and it's beautiful now. Plus, all my kids grew up on it. Glad I still have it.
That's another thing. It's fiberglass and a motor. If you can find one that has never sat outside in the elements, even covered, and has been well maintained, it doesn't matter much how old it is. Bargains to be had there. It was about 4K to tear out the interior and replace it all. Looks like new.
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ETA: I picked Baja because I believed it was super well built. In the 24 years I've had it, I have not been disappointed. I bet mechanically, it hasn't cost me more than $2K in 24 years. Shift assy had to be replaced last year. Backfired once (my bad), broke an exhaust flap and drank seawater into the block (thankfully, I acted quick and it was an easy fix). Other than that, I had to replace the cables and hoses to the outdrive (dry rot) recently and every 5 years I have the outdrive inspected. Pretty damn cheap to run.
This 2006 Baja H2X would fit most of your requirements, except not so good for wakeboarding. You really want a ballast boat if you're going to do serious wakeboarding. And some skill pulling a skier. You can pretty much rip arms out of sockets with this 320hp beast.