Is there a grammatical difference with this IDO pronoun then possessive pronoun, or vice versa?

When you ask for "grammatical difference," you have assumed that both are grammatical and "correct." So, let's set that Q aside.

Pragmatics: The order follows an implied order of significance: "Rewarding experience for A, (and of course, to some extent,) B." Accordingly, you decide what comes first.

In a specific case where one of the two words is the first person personal pronoun, it is advised that it always come latter, not before. "It helps both you and me," not "It helps both me and you."