The draft issue is at least partially fixed with the new cap rules, but there is still an onus on the Sox organization to pick the best players, and not the most signable ones, and really invest in how those players are developed.
I've railed year after year about the lack of investment in the big league team, but considering that the two years Jerry did that (2006 and 2010) didn't especially work out, I can understand why the Sox would be gunshy to splash the cash and threaten the profit margin. Also, they were a high bidder on Torii Hunter in 2008 and couldn't close the deal. Not sure if that's a plus or minus.
Also as far as new ownership goes, as a fan you really don't know what you're gonna get - and what you get could change over time. As an Astros fan, I initially loved Drayton McLane as an owner, but he turned into a meddler who wouldn't spend on prospects but would waste millions on a fading player like Miguel Tejada, and that turned me sour. Now the Astros are stuck with Crane who seems worse.
Jerry despite his pre-2000 faults has turned into a decent owner. Not perfect, or someone pushing the club forward like Arte Moreno of the Angels, but decent. What happens when Jerry sells or bequeaths the Sox is going to be the big story of the Sox in the next decade or two.
My hope for the near future of the Sox is that Rick Hahn as GM can make some moves to give us that talented dynamic young core that we've been lacking, both through player development (we have a very nice group of OFs in the minors) and trading for/signing top younger talent and trading away players who aren't getting it done for younger players with more upside that those we're trading.
Once the Konerko, Dunn, Rios and Peavy contracts are through, he'll have a ton of financial flexibility to work with to fill in gaps with good players, even if Jerry pares payroll back from where it is now (Our 4th or 5th highest ever by my count).
So I'm hopeful that the Sox will be better than they are now within 2-3 years given that the right moves are made, and I'm willing to sit through a few seasons around and below .500 if we get there.