They fly a ton. They have Beech 99s, Cessna 402s, and 2 Cessna 206s. One 206 has boots, the other does not. Since the last time I've been around that ramp, I believe they've gotten rid of their Beech 18 and added a King Air 90 for pax service. They have also added a King Air 200 and Beech 1900 looks like.
Chip runs the company as a micro-manager. If you are a good worker in his eyes, he will bend over backwards for you. If you are not the worker he desires, he will probably be the worst boss you ever had. I've flown with two of his former Chief Pilots and they both said that he liked them until they wanted to move on to another company.
The m/x I've heard mainly "stories" about. My brother, a FedEx mechanic, has a friend that used to work for them. I've heard a few stories...not willing to divulge, but I'm sure it's nothing different than what I've heard about other operators of the same caliber.
There was a crash of a Beech 99 a few years back. The story goes like this- The pilot was at an outstation and looked at his fuel situation and didn't think he had enough fuel to return to MKE. He called in and told the company this. Chip said there will be no refueling at the outstation. So, the pilot took off without refueling (wtf?!) The 99 ended up flaming out and landing a 1/4 mile short of 19R at MKE. Surprisingly the pilot was back on the line not too long after that and was fired on his first day back for forgetting to open the nose baggage door for the rampers. Chip takes his contract with UPS very serious.
All that being said, I asked him for a job back when I had 1150 hours TT. He said he would hire someone at 1200 TT for the 206 on demand stuff. He occassionally hires directly into the 99s depending on need.