I'm getting an error every time i try to upload, is uploading down right now?
Uploading has been crappy the whole year, at least for me.
Should i try and just reduce the size?
I don't think that would be of much help, even uploading pictures that are less than a megabyte take several tries sometimes, it gets worse a some hours of the day though some it's not 100% bad all the time, it sometimes is 80% bad, 20% bad, but I wish you luck with your uploads.
Try uploading with a different browser?
Furthermore, some parts of USA and Mexico tend to get timeouts at Iwara because of low upload speeds on the local ISP in USA or Mexico.
Try uploading from a friend's home, if your friend has a different ISP?
with 413, it means you are not able to send such file size. in this case it could be caused by client optimization or vpn