Ok so you seem to have some good points in there, let me explain the way we do it at Funnelish and in some side businesses.
We usually have two lists in ActiveCampaign:
A. “Product Name” - Leads
B. “Product Name” - Buyers
That’s it, the structure above has been proven to work for us in about all scenarios.
So let’s assume we want to find the ones who “DIDN’T” purchase anything (of that product or funnel).
Those would be the “Product Name” - Leads excluding “Product Name” - Buyers.
So in ActiveCampaign, you can have two automations (using the cart abandonment templates they have).
You’ll need to create at least one automation, but preferably two, like this:
-
Automation for people that enter the list “Product Name” - Buyers, If someone enters this list it means it’s a buyer so should notify them ASAP of their purchase confirmation. and then in few days send then an automation saying your order has been shipped out… if you want to provide tracking numbers it’s a bit of a hustle so I don’t personally do it till they ask for it.
-
Automation for people that enter the list “Product Name” - Leads, This one is a bit tricky, since it might take your customers a while to do the purchase, thus this automation always starts with a “Wait” timer for 30mins at least… After 30mins do not send them the email of cart recovery instead… check first if the lead you have exists in the Buyers list, if it does that means they bought already within the 30mins wait and the automation should end (and the Buyers automation will trigger).
Otherwise if they don’t exists in the Buyers list, that means they didn’t purchase, then you can keep bothering them with emails on daily basis, but before sending each email check whether they exist on the Buyers list or not, if the do “End the automation”…
And that’s really it,
Btw… All the above, is just a thorough explanation of what ActiveCampaign Cart Abandonment template already does! you can have that setup literally in 2 minutes… Explaining how it works takes longer than actually doing it.
And yes the second screenshot you sent is the one that should be used… not the first… you should set an automation on each and every single product…
But luckily, you don’t have to have that many products 
just use the variations from Funnelish for each product, that will make your life much easier.