TBH, 5e hates secret roles. (yes, i know this is not a 5e specific post, just a personal gripe)
There are way too many abilities that trigger on a failed roll or can be used after a roll that this kind of play style straight up conflicts with.
One of the worst ones for this kind of thing is the soulknife rogue's Psi-bolstered knack (that they get at level 3), with both triggers explicitly on a failed roll and refunds if the extra dice if it doesnt make it succeed so you cant even include mystery if the reroll made it a success.
