"so I have to spend $600 on a set of shocks to see if I can get a less stiffer ride?lol"
It's been that way pretty much forever. The stock shocks, even on Harley's most expensive bikes, are not world class quality. They are production shocks, made to fit a cost objective for the company. In many cases in the old days they were just the cheapest things they could install to hold the rear end up, short of solid struts. I'm not saying it's right, I'm just saying it is what it is. Btw, did you realize that all the other stuff on that $40k bike are also not exactly top of the line components? Or are you like many others who mistakenly believe CVO's are made exclusively with Screamin' Eagle parts? Nope, you don't get the fancy billet cam plate and oil pump, you get the same parts found in all other Twin Cam engines. There are many other examples but I won't bore you listing them. A CVO is just a high priced (and overpriced IMHO) option package like those you find at all car companies. They aren't even exclusive these days, considering they are built on the same assembly line as the lowest priced model and in larger and larger quantities.
If you consider the short amount of actual travel on the rear of the bike, even the highest priced shock on the market isn't going to make a Street Glide ride like an old Cadillac (floating over bumps, or as some of us used to say, wallowing all over the road). It's one of the many tradeoffs people make, style over function. And btw, $600 is just the entry level for upgraded shocks. Don't ask the guys what they've spent on the really good stuff like Ohlins, or other even higher priced products.
Jerry