Joe- yes, she does pay for those amenities and requests. In contract negotiations, the rider is presented, and the promoter and Artist management decide on the Artist's fees and then how much will be deducted for all the items off of that number. You can "rent" a band as long as you have enough cash to do it- anybody can...
For artists that don't tour their own sound and lights, the cost of the Rider comes off the top. Want a case of Crystal (seen it- most rappers couldn't figure out why they didn't get paid at the end of the night)? You, the Artist, will be paying for it. A typical hospitality rider will cost the artist $2-5Gs a day for 3 squares for the crew and band, water, towels, liqour, a couple of runners and after-show takeout. Lights and sound are $5-15K per show depending on the production requirements. And I have paid Union Labor bills in New York that have been $20K+ for a crew of 15. Now you know why a concert ticket costs so much. The Artist is Contracted at anywhere from $35-200K per show, depending on venue size and popularity. The promoter will take 10-35% on the Artist's merchandise, and takes ALL of the Parking and Concessions in 90% of shows. The Artist also pays the touring personnel- weekly salarys range from $800 to $4K for crew members, and $2-7K for band members. Each.
Nobody goes away broke from these things, except for the public. That is why we try to put on a great show- if you suck once, the paying audience won't be coming back.
As far as trucking is concerned, it is no different than any other company shipping its goods over-the-road every day... Fuel runs about $500 per vehicle every night, plus vehicle rental and drivers salaries, I always figure about a Grand a day per vehicle, taking into account fuel being $3 in one state and $2.50 somewhere else.. Pilot Truck Stops are my friend!!!
And when you see a musician or actor or athlete tooling around in some vehicle on TV, don't always belive that the car they're in is their own (or the house, for that matter).. When I worked with Foreigner, Mick Jones would love to ride Harleys on his day off. Our Tour Manager's job was to find him one wherever he could, and it would only cost him an autographed photo of Mick sitting on the bike in front of some Harley shop. If she owns a Vette, she is pretty smart (good investment), but more likely than not, it was a loaner for the interview suggested by some Production Director for the interview.
Once again, if Sheryl (or any other public figure, politicians included) wants to stand on her soap box and preach, she may OR may not have a clue about what she's talking about it... like MOST people. Still no laws out there that says you have to listen to them or agree that they are right.