Hi beegee thats a simple question to answer,first look for a boat that is in good shape,no damage to the hull, drive unit has not hit bottom,owner has taken care of it etc etc,also think of some kind of bimini to get out of the sun, it can ruin a day on the water as fast as a bad day can,think of the swim platform, is it wide enough to cover the drive,I had a customer fall off his boat and catch the drive only to end up with a 150 stitches from his ankle to his crotch,if you find a good used boat and the platform is too small check out www.swimplatforms.com, now for power, the old saying is always true GO BIG OR GO HOME,if you think about the power you have to get all that weight plus pull a skier a tube plus fuel plus gear, see where I'm going here, you need enough SNORT to get things moving, also think about if you need parts for repairs look at the dealers in your area, and how long they have been around? I have always been partial to Bayliner ,always had good luck with them, parts are easy to get and they are priced right,lots of dealers around, I spent $80g on mine, my friend just bought a boat for $400g and we both go and sit in the same place, only mine was $320g cheaper, and believe it or not I have more room on mine, hope this helps have fun and good luck :-)