membership rules when product is in cart to non members

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I have a membership product which and a set of membership rule (discounted price, and a custom shipping handler module which comes in for members). Problem is how to give these set of rules to customers just like they are given to members. Point is they add this membership product to cart and want to get discounted things on the same cart while they are not yet member but going to become after order will be confirmed. Checking out twice is cumbersome. Please give best strategy in a way that all other rules are already active for members. I was thinking of just changing guest users role when it adds that membership product to cart. Will this approach be buggy.

note that member is place in different group using magento customer group feature. 1. guest user has a different price for same product compared to groupmember 2. another discount is based on quantity and is in percentage. percentage is calculated on initial price by the group customer is in. 3. A logged in member can be in general group and add this special product to become member while checking out. 4. special shipping rates based on zip codes to both types of member is also calculated on checkout page.

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Create a shopping cart rule for Not Logged in user. Follow below steps:

catalog -> attributes -> manage attributes

Search for the ‘SKU’ attribute and set the drop down ‘Use for Promo Rule Conditions’ on YES.

On left sidebar, click Conditions tab

Click + button icon

Select Product attribute combination

Click + button icon

Select SKU

Now, you will see SKU is ...

Put your product SKU over there