Need help with what plugin I should get

I was looking for a similar thing a while back – found this: https://wordpress.org/plugins/order-attachments-for-woocommerce/

Hello,

I need to be able to send custom files to a customer for their order. Is there a great mod for this.? I am selling custom graphics so when they order a Logo I will need to send it to them a few days later

The extension below looks is able to manage that model you described:

• File Upload for WooCommerce

It will permit to your customers to access/change their files after purchase. If the product doesn’t work according to your needs, we are more than happy to offer a full refund (The timeframe is 30 days). This is in accordance with our refund policy.

I hope this helps.