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Moe,
All very reasonable -- and I don't disagree with anything ... EXCEPT "Make a bold move at 1B."
This team, to this point, has more or less proven the point I've been making for over a year.  That is a bad, bad, bad, bad, bad idea to BEGIN a rebuilding cycle with an expensive (bold) move.  That is precisely what Bavasi did with the Beltre/Sexson tag-team.  That choice influenced (and limited) every move that followed for 5 years.
The ChiSox currently have THREE of the top 12 hitters in the AL, and have a below average offense.  ONE big bat will be 1/3 as capable of moving the Seattle offense forward. 
I'm not saying the club has to keep Kotch.  I'm saying that ORDER matters. 
Even though the Bedard choice didn't work out -- it was reasonably well timed to the extent that the club "thought" it was the FINAL piece needed.  (They were wrong).  But, trading Kotch's 75 OPS+ for some 8-figure 140 OPS+ (assuming you have enough on the farm to pull it off) - only raises the TEAM OPS+ from 80 to 83.  Where do you get the other 15+ points of OPS to reach average?
If the answer is -- "Well, Figgy and Lopez will come around," then my response is:  AFTER they come around, talk to me.  If they start producing, and Kotch doesn't - (and we've got a warm body posting a 90 OPS+ in the DH slot) - I'll be THRILLED to discuss benching, trading, demoting, roasting, skewering and sauteeing of Kotchman. 
Personally - I disagree with the concept that 1B (Kotchman) is *ANY* easier to replace than Figgy and Lopey.  We had Sexson flaming out at 1B for two years and WHO were the "easy" replacements?
Anyone remember Cairo -- the guy who finished 2nd to Sexson in 1B starts in 2008, (while posting a .646 OPS).  The #3 1B that season was LaHari - who finished at .661.
Now - if by "easy" you mean -- it is easy to find a 75 OPS+ 1B to replace your current 75 OPS+ 1B -- okay, cannot argue with that.  I'm a Braves fan.  Who were the final 5 first basemen the Braves employed in the final 5 years of their playoff run?  From 2001-2005?
Rico Brogna / Wes Helms  (OPS+ of 62 / 87)
Julio Franco (94)
Robert Fick (95)
Adam LaRoche (108)
Adam LaRoche (100)
Those teams made the playoffs.  What followed in the non-playoff years?
Adam LaRoche (130)
Scott Thorman (67) - Craig Wilson (49) -- then traded for 54 games of Tex (161)
Teixeira (137) - then Kotchman (73)
Kotchman (103) - then LaRoche (152 in 57 games)
Troy Glaus (114) -- ( team is 19-20 and in 4th place)
The Ms could've gone out and snagged Troy Glaus, I suppose.  But I didn't hear anybody suggest him prior to Kotchman.  (They did suggest Carlos Pena). 
But a BOLD move is going to likely cost money and prospects.  And even if the Ms do geta "Big Bat" - they'll have 1/3 the number of big bats that the ChiSox currently have.  It won't matter without the other bats producing.
What I would dearly love?  I'd love to see Figgy with an OBP of .390 -- Lopez hitting at a 20-HR pace, Kotchman posting the expected .750 OPS -- and THEN the club brings in Dunn to DH.  If you're getting 90 and over OPS+ from everywhere except SS and Catcher, I'd be just fine with dealing Kotchman for an uber-bat at 1B.  THEN, you make a bold move.