Hi,
I think it's somewhat possible.
In that case, you need to configure one manual shipping method for each price point with the shipping cost entered in its "price" setting. And in each shipping method, you need to activate the "shipping price per product" setting.
Then, in each product edit form, you'll have an extra area "shipping prices".
In the Item 1, you want to block the 10€ and 20€ shipping methods.
In the Item 2, you don't want to do anything there.
In the Item 3, you want to block the 10€ shipping method.
That way, on the checkout, a shipping method will only appear if no products in the cart block it.
The problem with this is that if for example you have only Item 2 in the cart, all three shipping methods will be available.
One way to go about it to make sure that the shipping methods are ordered from the cheapest to the most costly and turn on the "real only" setting of the "shipping" view in the checkout workflow. That way, only the cheapest available shipping method will be selected and the others won't show up.
However, there is a catch:
- if you add Item 1, the shipping cost will be 50€ as that's the only one available
- if you then add Item 2, the shipping cost will still be 50€ as that's still the only one available
- if you remove Item 1, the shipping cost will still be 50€ as all three shipping methods are available and the 50€ was already selected before.
It would require the development of a small plugin to reset the shipping method selected each time a product is removed from the cart and then it should work like someone would expect.