The answer that claims that create_upload_url can only accept one file per upload above is wrong. You can upload multiple files in a single upload and this is the way you should be approaching your problem.
That being said, there was a reliability problem when doing a batch upload that was worked on and fixed around a year or so ago. If possible I would suggest keeping the batch sizes a little smaller (say 100 or so files in a batch). Each file in the batch results in a write to the datastore to record the blob key so 1744 files == 1744 writes and if one of them fails then your entire upload will fail.
If you give me the app_id I can take a look at what might be going wrong with your uploads.