that's why i said just try it. this way there is no risk at all.
don't go buy new equipment or anything. if it doesn't work you just go back to what you were already doing and no loss at all.
don't count on the money and start buying new equipment and hiring a crew or anything.
if they wanna pay you once a month or something tell them they have to pay you at the first of the month before you do anything. tell them you can't go cut 60 yards without getting paid a dime. tell them all of the expenses that are involved cutting 60 yards like gas, blades, trimmer line, etc. etc.
accept nothing less than getting paid upfront that way you don't go cut 60 yards for free because they don't pay in time or anything like that.