Most good dealers should let you buy a ski and then exchange it if you don't like it. Just make sure you keep it in good shape.
And ask them before you buy.

Check ski magazines for reviews depending on your style of skiing, arc or hook-and-pull.

Most of your quicker turning skis do not like to go straight so they normally feel a little snakey in the bubbles. Don't let that drive your choice.

I would avoid the really expensive top end skis. I don't think they are worth it for most recreational skiers.
Got to Ski Limited or Overtons and see what they recommend for skiing ability.

I think dual boots are over rated. I currently ski at 15 off at 32-34 mph and have not felt the need for them yet. But who knows, maybe if I tried it I would love it...
A lot of non-tournament boats have a hard time pulling a bigger person out of the water with both feet in.

As far as the wing goes. If you do not know about deceleration then you could probably take it off. If you are still skiing on long line you definitely do not need it.

Good luck
Dave