I'll give my 2 cents based on the OP's structure.
1) The Major League roster definitely needs some tuning, particularly with the bench. I think one of the reasons the lineup ran out of gas was because we weren't deep enough, so Robin was forced to ride his main horses nearly every day. Faced with losing Youk and AJ to free agency, it might become a moot point if we can't solidify their respective positions. Still, find some second-tier players who can hit and hopefully, we won't see another September drought on offense as we have these past two weeks. Consider Santiago as the fifth starter if no one can be picked up via trade or free agency. The bullpen is fine as it is if you subtract a lot of the September call-ups. I like what the future holds for the pitching staff overall. A lot of good young arms to build around.
2) The farm system definitely needs a major overhaul. I won't pretend to know how to execute that because I'm not a big-league GM. However, if getting fresh young blood down in Charlotte and Birmingham means trading away some of our higher-value Major Leaguers, I wouldn't be against it. This is an issue that has plagued the Sox for years and why we've constantly had to look for outside help instead of shaping more of our roster internally. I agree that KW may have overdone trading prospects for established veterans, but we'll see if Hahn decides to be more conservative in that regard. Hope the drafting continues to improve as well.
3) I don't know if Brooks Boyer needs to step aside, but there needs to be a new approach in how this team is marketed. Dynamic and parking prices are issues indeed, but the bigger one is that they need to show people why taking a trip to the South Side is a good idea. We were in first place most of the year and Boyer failed miserably in taking advantage of that fact. Otherwise, we would have broken the 30,000 mark much more frequently. Alas, that wasn't the case and that resulted in the usual tired "Sox fans aren't showing up" crap from the media. Something needs to be done badly. Also, do away with a lot of the promotions and create new ones. All the buzz from 2005 is gone, so you don't need to act like it's still there by keeping everything from that year around. Everyone else has moved on. They need to do the same.
4) Hawk and Farmer aren't going anywhere. That much is certain. I wouldn't be surprised to see Stone jump ship and regardless of who you pair Hawk with in the booth, the TV broadcasts are always going to sound the same because he's the one dictating how it goes. Get rid of Jackson though. The quality in radio broadcasts took a big hit after Stone left and Jackson is hardly an improvement over Singleton (whom I will give props for making it to ESPN). We've heard time and again how boring it is for the listening audience and I can't say I blame them. There's no excitement there and if I weren't a Sox fan, I'd probably bash it endlessly myself. Farmer can sound good. You just need to pair him with the right guy. Maybe Wimpy? Just a name I'm throwing out there. Just take that with a grain of salt. Help draw the fans in by making them want to listen to the radio instead of putting up with Hawk if that's not what they'd rather do.
Farm system wanted
Top prospects now being accepted at 333 W. 35th Street, Chicago