I get your point, but I look at it from a different angle, because I'm a fan of a small market team.
I find it really interesting how Sox fans are so hung up on how much team payroll is year after year. Its really unique to Sox fans and I think they go a little overboard about it, TBH. Sure they can overpay for a guy like Bregman and jack the payroll a little more, but then if he gets injured, or struggles we're back to having the conversations you're currently having about Story and Yoshida and how they're overpaid. Its kind of a no-win situation. As for ticket prices, sure they're high. But to be honest, everything is freaking expensive in New England....I don't think that's specific to the Red Sox. Curious to see where the Pats, Celtics and Bruins rank as well.
My perspective is that at the end of the day, teams should try to assemble the best possible talent at the best value that they can (unless you're the Dodgers and are out to ruin MLB's salary structure). The definition of "value" is highly variable though. But then, that's why we have discussion boards.....