You can contact the Clerf of the Court in the jurisdiction where they were prosecuted and convicted. Ask to see the "Judgement and Commitment Order". This is where the lawyers go to get their documents filed and research the filings in the case. There might be a nominal fee to print out any information you are requesting.

There is more than one penal facility in Leavenworth (county, federal and military). The federal side has two separate facilities for different custody levels. The satellite prison camp is adjacent to the US Penitentiary and is by far a better location to have to do time.

He will do 85% of the 60 months (51 months). Every hour spent in confinement will go towards fulfilling this commitment order no matter the facility he's held in. 

This is not a good scenario. The DUI could cost him a lot more time behind the wall, probably not "life", but if there were any injuries or property damage it could be significant time.

Possession of a controlled substance less than 1 gram is a state jail felony with a punishment range of 6 months to 2 years state jail (no parole from state jail) and a fine of up to $10,000. Due to the overwhelming number of state jail dope cases, the law requires probation in many cases.

The designation for commitment is determined by the Department of Corrections. They will base the security classification on a number of factors including their criminal history, the type of crime they are convicted of, the value of the crime in dollars, was there any violence, and was anyone injured or any involvement with a gun. 

I did time in FCI Miami with a few guys that were caught off the coast smuggling immigrants and they got five years in federal. With a "bad past," it might be more because they use the negative history against you at sentencing.

You can contact the Clerk of the Court and request a Judgment and Commitment Order. This is the document that the judge signs and it has all of the sentencing information.

Depends on who he said it to and what his prior criminal history looks like. 

Depends on the mood of the judge that did the original sentencing. The worst case scenario is that the offender must finish out the remaining months on the original sentence.