Filing a suit on your own is very complex. In the upper court he would be entitled to a jury, but not in small claims, one must not only know how to form and caption a complaint, but respond to Motions, if filed, impanel a jury if he requests one, etc.
I have filed suits on my own outside small claims, but I don't even know how to impanel a jury without some consultation.
Go over it in your head and see if you will just settle for the 1,500.00 if it is a sure bet.

