Learning the ropes...
I've encountered a number of "set up" problems over the years, but have generally taken the approach of aggressively eliminating them in each future job.
So, we had one job where exact written instructions (and I did everything from giving exact "direction independent" instructions on how to get to the hotel (complete with map square information on the local locater map system) to specifically describing the route into the hotel) were not enough to keep my two older trombone players from getting lost. As a result of that, we now post "SOTSDO signs" that clearly indicate our assigned parking area, the case/change room, how to get into the venue from the designated entrance, and so on.
On another, the power went out to the circuit supplying the stand lights (but not the PA and the "piano" and other instrumental stuff). We never were able to find out where the breaker was for that particular outlet, and anything else into the working one would have overloaded that circuit. So, we ended up playing in semi darkness as a result. The next day, into the contract went a clause that the circuit breakers were to be pre-located during the initial walk-through of the venue.
In large part, the music business is a learn by doing environment. While decent music instruction is easy to come by (if somewhat wedded to the teacher-student method of learning), there is very little in print on how to do all of the stuff surrounding the operation of a musical group.
The AFM has done a little with the contracting side (although my contract is considerably more specific than the standard AFM one), but advice on how to maintain a music library, how to arbitrate disputes between members, how to set up the stage, how to configure and operate the sound system is thin on the ground indeed.
I'm an aggressive reader, and have consumed stuff ranging from 1920's big band orchestration books (thank you Amazon.com) to any number of obtuse and irrelevant books on sound systems. But, I still have not seen a decent book on live band theatrical lighting. (My college course on stagecraft was only marginally helpful.)
I did my bit in this arena by formulating and documenting the method that I follow to produce a band book. I think that a copy of it is found somewhere on this site, although I cannot tell you where; if it is not I would be glad to send it forward for inclusion. (The same can be said of my horn stand stuff; again the location is a mystery to me.)
Occasionally you can glean a little from biographies of band people. I got a couple of helpful hints out of Charlie Barnett's biography. But, by and large, those are long on booze and slease and short on any practical advice. Somebody ought to write a book...which few if any would buy if it was printed.
I've commanded half an armored cavalry platoon in combat in RVN on several occasions, but running the business and personnel side of a musical group, never mind the musical side of it, is far worse as far as bother is concerned. Not as hazardous, though...