I've asked this question before in Sept 2021 to no avail. The problem detailed then continues to exist at present. For background, here's the link to this closed discussion is included at the end of this post. In a nutshell, in Tax Planner, looking at Schedule E, Rents, the associated tax form line items is set to Schedule E:Rents Received, of which my Category "Rental Income" is associated. Despite the fact that I create a Business Invoice with a line item that has Category set to Rental Income, it will NOT carry to the Tax Planner. Doing same thing in a checking account register behaves likewise. It turns out that you need to also populate the Tag field with a Tag that has been designated as type Property. This begs the question as to why. The bigger problem is that when setting a tag in the Business module, tags with a Property type are not available (only Business type tags), rendering it impossible to get line items entered with a category associated with a Schedule E tax line to flow to the Tax Planner (you can, incidentally, select a property tag in the check register, which alleviates the problem for items originating there - not possible from an Invoice register, however). Bottom line is that it makes no sense to require a property type tag at all. If the user selects a category that is associated with a Tax Schedule E tax line, no matter what type of register (Checking, Invoice, A/R, A/P, etc.), it ought to flow to Schedule E in Tax Planner. Hopefully, someone from Quicken will weigh in on this. I really depend on accurate info in Tax Planner throughout the year to determine whether I need to make estimated payments, engage in loss harvesting, etc. Currently, I must remember to override Tax Planner (using User Entered) to populate all my Schedule E Income/Expense lines to get an accurate picture. Here's the link to my original post that explains somewhat in greater detail, and the various testing I did to try to ascertain what Quicken was actually doing "under the covers".
