Who will be most sorry about Demaree?

Though seemingly involving a technical ex post facto issue, the Seventh Circuit's ruling in Demaree could (and will?) have a profound impact on post-Booker sentencing (basics here).  At first blush, Demaree may seem like bad news for defendants: it says district courts may (and should?) apply the most recent version of the now-advisory guidelines even when they call for a longer sentence than the guidelines in place when the defendant committed his crime.  But, upon reflection, Demaree might also make judges, prosecutors and probation officers miserable because of the intricate questions the ruling raises. 

Here are just a few questions swirling around my brain after Demaree:

1.  Though Demaree says the ex post facto clause does not preclude a District Court from using the latest guidelines, it doesn't say whether a court should or must use the latest (harsher) guidelines.  May a district judge in the Seventh Circuit still decide, as a matter of policy, to "consider" only an earlier version of the guidelines?  If a judge does rely on an earlier version of the guidelines, does a within-guideline sentence still garner a presumption of reasonableness?  Or, is reliance on any old version of the guidelines per se unreasonable?

2.  For counsel and probation departments, Demaree issues arise well before the day of sentencing.  Should PSRs throughout the Seventh Circuit now only calculate ranges based on the current version of the guidelines even if they are much harsher (e.g., in fraud cases) than the version in place at the time of the crime?  Can prosecutors and defendants stipulate in a plea agreement that only an earlier version of the guidelines should apply?

3.  Will Main Justice, which has argued against the Demaree rule, seek en banc or Supreme Court review ASAP?  In the meantime, must prosecutors in the Seventh Circuit only argue in favor of the current guidelines?  Will prosecutors contend on appeal that only the current guidelines should garner the presumption of reasonableness?  How will main Justice handle this issue when it comes up in other circuits?

4.  Isn't the Seventh Circuit's recent ugly Jointer ruling mandating that the crack guidelines be followed (details here) wildly inconsistent with Demaree?   Demaree stresses that a sentencing judge after Booker need only "consider the guidelines and make sure that the sentence he gives is within the statutory range and consistent with the sentencing factors listed in 18 U.S.C. § 3553(a)."  It also says that a district court's freedom to impose a non-guideline sentence is "unfettered" and subject "to only light appellate review."  Finally, Demaree says a sentencing judge "is certainly entitled to take advice from the Sentencing Commission."

In Jointer, the district judge considered the crack guidelines, followed the USSC's advice that those guidelines are too harsh for low-level dealers, and then exercised his supposedly "unfettered" freedom to impose a (non-guideline) sentence of 7+ years for minor drug sales.  Yet, even though that sentence seems entirely "consistent with the sentencing factors listed in 18 U.S.C. § 3553(a)," the application of purportedly "light appellate review" in the Seventh Circuit resulted in reversal.  Looking at Demaree and Jointer, which were decided only days apart, I must quote an early era computer: "Does not compute, does not compute, does not compute......"