With-out seeing your machine and what it has for chain points, what I would do is wrap the chain around the axle tubes, hooking the chain to it's self then attach to the opposite side of the trailer. When finished both the front and rear chains should form an “X” across the deck of the trailer. Also, make sure you pull over after the first mile or so and re-tighten the chains, as rubber tired machines are notorious for bouncing loose, but after a re-tighten seem to hold put quite well. I always use four chains and four binders, and don't forget to bungey or wire the binders closed. Also, around here to be legal you should be using grade 70 transport chain and hooks.
Something to consider with your trailer is that the weight really adds up fast. On my 14000lbs trailer almost 2500lbs is used just in the weight of the trailer it's self, add a skid and a couple attachments and suddenly there isn't much available gvw left over. Also what is your tow vehicle rated for? Being legal sure isn't cheap, no matter how you look at it.
Hope some of this helps some or atleast makes a little sense.