As someone who has owned a 96 Challenger for the past 6 years...this is not your boat for skiing...I'm 6' 195 lbs...I tried to slalom behind this boat...not happening! It will pull 2-3 adults on my three person tube and you can kneeboard behind it, but definitely not your boat for skiing. I don't know if it's that the boat is underpowered, 110hp is pretty good for this size boat...I think it has more to do with the limitations of the (in my opinion) small jet pump diameter and horrible performance of the OEM impeller (11/25* pitch with square leading edges). It's almost like having a car with a lot of power and skinny little tires...you've got the power...you just can't "hook it up"...
If you do decide to get the 96 Challenger...put a Skat Trak 14.5/22.5 impeller in it...that will give you your best hole-shot (without cavitating like the OEM impeller will do at hole-shot) and low end to pull with, without sacrificing top end...