A buddy of mine used to work for a place as a salesman and he spent $10,000 on a dinner for something like 15-20 people probably 20 years ago. He said the bill was half liquor, half food. The worst part? The food was the incredibly fancy but REALLY tiny portions, so he ended up leaving hungry and sober and had to stop at a fast food restaurant on the way home to not go home hungry.
When he sheepishly turned the bill in to his boss, his boss looked at him and said "You brought Client X to THIS restaurant and spent $10,000???? You got off CHEAP! Last time I took them, we spent closer to $20,000!".
I mean, if the guy is expensing $500 hotels in Indianapolis on a random weekday, he should rethink where he stays. But when you are in a town for an event, sometimes you gotta pay what you gotta pay.
For example, what if the $300 a night hotel meant he didn't need a rental car? Maybe saving the gas and parking and rental fees pays for the difference between that and the next less expensive hotel.
And a steak dinner - oh my, stop the presses! Next time, take the potential donor to Applebee's and insist they order a meal less than $10. And don't let them upgrade from fries to onion rings, whatever you do!!!!!!