A buddy ask me what i thought . Long story but he drives part time for a amish that owns a f350 and 20' goseneck. The amish is moveing so he will lose this job. My buddy is going to get a settlement and wants to buy a pickup and goseneck. He dosent have any thing lined up for it . The job he has now is the cream of the crop he dosent work over 6 hours a day the amish is a great guy very clean and has been out in the world. He has another job that takes him out of state some. He wants to buy something 3 years old or newer.
Sounds like he wants to keep working at a job he likes. Ask him if the work he does now will be available when his boss leaves. Then he has to make a business case. Will it pencil out with fuel, insurance, repairs, etc.? Remind him he really wants to start his own business not be an employee. Otherwise he'll be stuck with equipment costs and no work.