Insightly: Can I file uploaded in JotForm also be uploaded to Insightly?

2.  Can a file uploaded into a JOTFORM, that is then integrated to Insightly as a Contact, be uploaded at the same time with a single integration, or is there another way to do accomplish this?

When you map the uploads field from your JotForm in your Insightly account you will not get the upload uploaded, but you will have the link to the file instead so each time your form is submitted with an uploaded file the link will be sent, here is an example about the link that will be sent: https://www.jotform.com/uploads/Kevin_G/53068447185967/343621286442295573/SampleImages.jpg 

I would suggest you to give it a try and let us know the result of your test.