"In this case, the timing of a check for a small amount doesn't bother me."

It's Payroll related. You need to be concerned, if you are trying to teach clients how it works. It's not reimbursement for a ream of printer paper.

I always have a bit of concern for things that don't make sequential sense, when it is discoverable (documented and reported). It's a very slippery slope. They'll play the game of Telephone with any edgy guidance. "I was told I could put it on the check, even if the reimbursement isn't made until later." "I was told to include all the amounts in this year, even if some isn't paid until next year." "I was told that as long as I pay myself for it, I could take it off my taxes, even if it turns out this policy doesn't qualify or I no longer have that coverage."

"I was told..." is where they take bad guidance and make it worse. And they are not the professional that started the landslide or misconception. They are just trying to maximize it to their benefit.