There are many different ways to make money flipping trailers. One way is to buy a trailer and sell it at the end of its life cycle, which can take anywhere between 2-6 months depending on how often you advertise your business. Another way is by trucking in used trailers from other states that might have been sitting around for years, then selling them as near new or refurbished units at an increased cost when theyre worth more than their original purchase price.