Add upload field to checkout form

I’m trying to add a file upload to the checkout process. I can add a field just fine, however actually getting it to upload is another issue. It seems ajax and file uploads don’t play well together. Is there a solution for this?

I was thinking I could do two separate ajax calls on the checkout, one for woocommerce and one for my upload. That’s resource heavy and might be slow though. Plus I can tie the validation stuff together then which might be a pain.

Just looking for any other options!