Rebecca Cunningham departed from a family of snobs. Her father was a snob, Her mother was a snob, you get the idea. Since Rebecca is not investing in a snobbish business, she combines her history of snobbish with her business. For example in "A Touch of Glass", Rebecca is excited about 2 escaped convicts. They talk funny and obviously is trying to deploy a scam. Even Baloo figured. Rebecca took one look at Muffy and Buffy's smart clothes and identfied them as rich people. I quote " Don't judge a bankbook by it's cover" Rebecca is learning her lessons, and becoming more realistic everyday

Rebecca attended business school, and after she earned her master's degree, Her father helped her start a business, but it failed after it exhausted finacally.Then she discoverd a place named "Baloo's Air Services", she enterd the dingly building, and found out that Baloo couldn't afford to run the business and will not be able to keep his beloved Sea Duck. Rebecca paid for the plane and bought the office, since she had no flying experience, she agreed to hire Baloo and let him fly the plane until he buys it off.....eventually.
Since Baloo is a lazy and slow bum, He always go to Louie's after his runs of picking and delivering cargo . Baloo always comes back with excuses. Rebecca get so mad and make all kinds of threats, yet she never found it in her heart to fire Baloo. To her, Baloo is a good friend, plus Baloo is a good male role model for Rebecca's daugher, Molly. Rebecca is a devoted mother to Molly, but the concepts of a busy office seems to overwhelm her attention with Molly. But Rebecca always make it up.

Rebecca might be plotting a way to earn more customers, or figuring out how to spend time with Molly. In sincere, I think Rebecca is a sucessful manager. She is the heart and souls of higher for hire.