Hi @bard95,

So I’m not sure I’m fully comprehending the original scenarios that are presented but based off of how I’m processing the information you provided, my recommendation would be to add date criteria to your segment.

For example, for a net new buyer who has absolutely no placed order events prior to making their first purchase, I think you could create a segment with the definition of has placed order equals 1 over all time. The part where I may be confused of is the second purchase where you refer to your upsell page and a customer placing a second order but still being a new customer. Does this mean that they are placing two orders in the same day? If that is the case you may want to use a definition such as placed order is at least 1 in the last x days. Where x is the number of days where you still consider somebody a new buyer based on their purchase dates. 

For a repeat buyer, you could use something like someone has placed order is at least 2 over all time and add in additional criteria that makes sense: How to Create a Repeat Purchaser Segment

Once again, just based off of how I read the post, that would be my recommendation but I could be off base here.