Kim writes: "These are all in addition to the technical issues . . . such as performance issues, reliability issues, and misrepresentation by the vendor of the systems capabilities . . . .  // I don't know of a great book or even article that describes this ..."

Perhaps have a look at retired IBM-er Robert Britcher's Limits of Software (1999) and esp. his chapter 16 "The System to End All" which describes the stupendously expensive FAA Advanced Automation System (1981--94).

"At $3.7 B, the AAS was one of the largest civilian computer contracts ever let . . . It was the largest single contract in IBM's history.  At its peak, the project employed more than 2000 people--about $1 million a day" (p. 171)

Best, Tom