With 2 walkbehinds alone, you may be over loading the trailer if it is rated at 2000lb gvw! I don't know how wide the trailer is, but if you are not overloaded with the equipment you own, if you put the two walkbehinds back to back, you may balance her out so that you do not overload the tonge. I would make sure to have some good safty chains as back up. 200lb tonge weight does not allow for much at all. Maybe you need a new hitch and trailer or at least coupler. Think of the ballastic forces that you incur hitting bumps and such in the road, that 200 + lb load can be magnified to a very heavy load that could jeporadize the safty of those on the road with you. Better Safe then sorry.