I am — sadly — well aware of the “solution” for dealing with vendors and customers being the same person/entity. This is not a request for help in finding a solution. 

Instead, it is an observation. From someone who is a highly-skilled programmer and database designer. 

The fact this situation isn’t handled intuitively is a huge, dinosaur-killing-level blunder on the part of Quicken. Accounting is supposed to represent the real world. In the real world individual entities can fulfill many roles. Quicken attempts to be accounting software. Consequently, this “problem” should’ve been addressed in the earliest architectural discussions for the Quickbooks database. 

It was not. 

Shame on Quicken management for letting this flaw exist. But anyone can make a mistake. 

The real nastiness is that Quicken management cares so little about their customers that they haven’t made fixing the problem a AAA don’t-go-home-until-it’s-fixed priority. 

Which makes it abundantly clear Quicken does not care about their customers.