Membership Pricing

Hi, could you tell me if your PlugIn could provide the following case:

By now, only Logged-In and registered/paying members can buy products in our shop (www.purefoodstore.de). We have to different memberships, a monthly and a yearly-one. We are using WooCom Memberships and -Subscriptions for that. As a guest you can´t buy anything, but you see the normale (high) price and the reduced Member-price.
We would like to open the store for non-members/guests, so that they can shop without a membership, paying the normal (higher) price. I guess thats possible, no? By defining rules wich role have to pay which price.
But more important would be, that guests can add products to their cart (with normal/high price) and as soon as they also add the monthly OR yearly membership to their cart (and buy it via checkout), the prices should drop down to the lower member-price,already in the cart.

Is that possible with your PlugIn?
Thanks a lot in advance!!