shipping only when option is selected

Hi there,
Is the following possible? I tried every combination of shipping but can't get it to work:

I have a product (online video), so no shipping required. So far so good, everything works.
This product has an product-option that people can select which is a collectors box. When this box is checked, i want to have two options visible during checkout: Eshop_item & Eshop free. (free means collect at shop, item means sending via analog mail.) 
When i set the send option in the product option to 'yes' nothing happens, also not in combination with other settings.

Hope to hear from you!
Regards, Martin

Dear Martin Boekhout,

Thank you for submitting the question here. Please submit a new ticket to EShop category to send me the super admin account to your site there so I can help you to check and find a solution for what you want.

Sincerely, Giang