If you loan someone several thousand dollars over a two year period..writing them several checks..can you file a small claims case and when that is fr

You can sue your friend for breach of contract in not repaying the loans within either the time agreed, or within a reasonable time.  You can do so in small claims court assuming no jurisdictional issues, i.e. many small claims courts do not allow suits against residents of other states; you would have to sue in a court of general jurisdiction.