What’s important when buying a fleet?

Please help me.  What are the 3-5 most important things you would tell someone thinking about buying their way into the trucking business? Why in the world is the T3—Technology Transforming Transportation™ guru asking a question like this?

One of my activities is to be a business mentor for SCORE.  This morning, I am headed to a meeting with a new mentee that has an opportunity to purchase a small trucking company with 2 trucks.  I don’t know a lot more at this point.  I believe the company has been in business for a few years, has positive cash flow, and some assets in trucks and trailers.  The CSA and safety records are a question mark. 

I expect one or more of you have been in this position in the past.  This is the American dream—to own your own business, perhaps employ others, be your own boss and travel the country.  Some of you have been successful at this type of endeavor and others have found it wasn’t their cup of java (do truck drivers drink tea?).  Let’s start a conversation.  Perhaps some of the programs to help the veterans with loans, driving licenses and such can be extended with your help through this conversation.