It's funny - I'm new to the club, having bought a 20 year old boat (with newer power).
I also own a Mercedes, and it's funny how the perception of the crowd treats them both. When I bought my truck, all I heard was 'it's a status symbol' and it was 'living off reputation'. I'm an engineer, and have always had a deep appreciation for products that are well engineered. I'm willing to pay more if I can tell the extra work was put in during the design and engineering phase. I've heard the phrase 'over engineered' very often, and I've yet to see anything that actually qualified as 'over engineered'.
The irony is that both were bought with the same factors in mind. Safety, security, stability. I didn't buy a Mercedes because I wanted to impress the women (if I did, I was an idiot, since I bought it after I got married). I bought it because at the time, SUVs rolling over was all the rage, and MB was the only one who did extensive rollover testing and built reinforced roof structures.
The Grady was the same deal. I wanted a hefty, heavy, solid boat. The best part was taking my 8 year old son with me to look at boats. At the insistence of a surveyor friend (who is also anti-Grady), we took a look at a newer Pro-Line. 'No wood, no rot'. I could practically feel the boat flexing under my weight, and I'm not all that fat. We walked away and I asked him for his impression, and he told me the boat reminded him of a rental car we got on vacation. No frills and cheap, and plastic all around. I also took him to see our Grady after I had made the initial deposit. He liked it, and asked me how much more it cost than the Pro-Line we saw. When I told them they were the same price, he said 'really, why?'. My sentiment exactly; the boat was a good 10 years older, but the sturdiness was apparent from the second we stepped onboard.
And just like the Mercedes, all I ever heard about was how they were unreliable, coasting on reputation, built sloppily, horror stories about people who were massively unhappy with them. To date, almost 11 years later, I've only replaced wear items on that car and it has never let me down once. Of course, I take loving care of the vehicle, and don't drive it like a jackass. I plan to do the same with our Grady, and only hope it turns out as well as our MB did.