How to configure multiple digital products with single access to a member site.

I am trying to setup a commerce site where a customer can purchase monthly access to an expert. The digital product enables access to the expert + access to a member site with additional premium content. There is only 1 premium content site available and access comes with all expert digital products. For example, if I setup three digital products for Expert 1 - John, Expert 2 - Harry, Expert 3 - Sue, all products get access to Member Site 1 via a "Member Site" in SquareSpace. So, instead of the digital products being "Basic, Advanced, Expert" it is more like "John, Harry, Sue" - you buy access to people experts...and get access to a member site with additional content. 

Before I commit to this, I want to make sure this setup will allow for the following use case:

Customer buys "Expert 1 - John" digital product on a monthly subscription. Customer then decides that they'd like to also buy "Expert 2 - Harry" digital product to also get access to Harry's expertise in addition to John's. Customer already accesses Member Site 1 through their subscription to "Expert 1- John".

If both Expert 1 and Expert 2 are digital products with access to Member Site 1, will squarespace allow the customer to buy "Harry - Expert 2" subscription after they previously purchased "Expert 1 - John" or will this create an error?

If the above is NOT the correct configuration, how would I setup squarespace to accommodate  this?