What you keep doing wrong is associating the payment as if it relates to anything other than:
It's a distribution.
That's all you have. An indirect distribution.
Then, the Beneficiary notices, "Hey! They spent what would have been considered Mine; and, by spending it for me, on something that would have been mine to pay, I get to treat it the same as if I paid it, which happens to be something that for my personal tax filing might show as a deductible itemization for Medical expense."
So, you have two Separate activities: Whether or not there was a Distribution. And whether or not there is something a person can include in their taxes.
Because your beneficiary had Two Events this year.
The Trust had one. That's where you keep stating this scenario incorrectly.
"Level Up" is a gaming function, not a real life function.