If you are new to expediting a small fleet owner may be willing to give you more personal attention but may not be available 24/7 if a major problem comes up. A small fleet owner may not have the cash flow for timely settlement payouts. If I were looking to drive for a fleet owner I would be more concerned with the condition/maintenance of the equipment, testimonials from former drivers, especially the ones that eventually bought their own trucks and the carrier the owner has trucks leased to.