For the 3+ decades I followed the Sox before JH, I always felt like ownership did "just enough" to keep the fans involved and thinking we had a chance, and we did a few years, but we never took that one or two extra steps to make it more of a surety. I don't think we were ever preseason favorites until the JH era.
It seemed like we were, many times, an ace away from being a top two or three contender. I seemed we lucked into Tiant, who brought us oh-so-close. The farm brought us to 1986, not any key signing. It wasn't until Dan D brought us Manny & Pedro, and then JH made that extra move of getting us Schilling that sealed the deal. He also got us key pieces like Foulke & Mueller, and later Beckett, Lowell and others, who all made us top 3-4 contenders for many years, even some we bombed out.
Under the DD era we saw what could be viewed as overkill building the 2018 roster, and we had damn good rosters in 2016 and 2017, too. (Even 2019 was very nice, on paper.) Then, poof.
Jh had cut back, several times, in the past, but not to this extent and for this long a period. Some of his major signings, like extensions to Sale, Nate and Devers, plus FA signings like Story and Yoshida fell short of replacing who we lost due to aging or money choices.
Now, we have a pretty nice core of young players, of which only Houck, Duran and Crawford have just started their arb years. We have a great set of prospects that are near ML ready and another set behind them that should be top 100 in a year or two and ML ready in 2-4 years. We are clearly at a place where 2-3 major additions can get us near the top 4-7 contender area and maybe 3-5 key additions away from being a top 2-4 contender.
I guess some disagree, but that is my opinion, and I feel we should get even stronger as our young players mature and our prospects make an impact. The time is now. Don't blow the window or shorten it by "waiting until next year!"