Firstly, I would like to thank everyone for their honest, straight forward, great non biased opinions. After doing some more research and comparing what I could get for similar money I came to a conclusion:
Today I drove 90 miles (instead of 1800) to look at a 88 TriStar 190 that has been owned by a fellow Ski Team alumni for the past 16 years. He bought it from a (at that point) 68 year old man that owned it from new. Fresh water only, well maintained, super clean and quiet original motor, original upholstery (some areas need a bit of work - 6 out of 10 rating), great trailer in excellent condition, 720 hrs on the hull and motor. Oxidized exterior with no serious nicks or dings (great gel coat condition), one soft spot in the floor right behind the motor (engine cover hinge area), and otherwise very good condition.
Bought it for $4700. I feel really good about the purchase and looking forward to getting her polished up looking great! I know the TriStar is not for everybody, but I have a wife and two kids (5 and 7) and feel that for the money I would be hard pressed to get another Mastercraft, let alone boat. Pics are from tonight with no work done.
Let me know what you think. Cheers!