Legal Question in Business Law in California

You may have two hurdles here. First, you cannot sue twice for invasion of the same primary right. If you have a right to collect commissions in May, you can sue for their nonpayment in July. Can you then sue for nonpayment of June in August? I think so, because each nonpayment is based on a different obligation.

Next, Small Claims has special rules as to the number of suits and total amount that can be demanded. See Code of Civil Procedure section 116.231. No person may file more than two suits per year in which the amount demanded exceeds $2,500.

The whole subject of claims splitting is fairly technical and an attorney would have to study the contract you will be suing on to see whether your are proposing impermissible splitting. My guess is no, but I'm not sure.

You can't split your claims. If you have damages in excess of small claims jurisdiction, you either waive those and sue in small claims, or get all of your damages in an action filed in unlimted civil or limited civil jurisdiction of the Superior Court. Courts and opposing counsel are not fond of people suing over and over again for the same thing. Once a contract is breached, it is breached. Get your damages and move on with your life.