I did a spot of research on the emoluments clause and found three instances where specific events were evaluated for breaching this clause:
1 - Theodore Roosevelt. Nobel Peace Prize. He accept both the cash award and the medal.
2 - Barack Obama. Nobel Peace Prize. He accepted only the medal.
... and most interestingly ...
3 - Ronald Reagan. Receipt of pension payments from the state of California as a former Governor and California pension plan participant.
https://www.justice.gov/sites/default/files/olc/opinions/198...
The way I read the analysis of Ronald Reagan's situation, any benefit from a domestic state, city, or county could potentially fall afoul of the emoluments clause. Think here of any local property tax rebate from a city to entice a Trump business to build a hotel or set up shop. Maybe even a tax rebate / waiver from prior business development agreement could fall afoul. Who knows how deep this particular rabbit hole could go.
I also was puzzling over Hobby Lobby the other day and I realized that Trump's situation vis-a-vie the emoluments clause could be parallel to Hobby Lobby versus the ACA. Hobby Lobby wanted out of the mandate for birth control and the Supreme Court sided with them because Hobby Lobby was a closely held corporation; close enough where the owners' religious beliefs could be infringed upon by ACA birth control mandates on the corporation they controlled.
I believe the Trump empire is a closely held corporation like Hobby Lobby. Per the Supreme Court a closely held corporation like Hobby Lobby has a personal connection unlike widely held corporation. Simply saying payments made to Trump's corporation is a sufficient separation from the person to avoid the emoluments clause may not be a strong argument for those arguing Trump's side.
Edit: IANAL, but rather a politics major.