How do I resolve RAW and 'common sense', with the phrase 'When you roll for initiative', when combined with initiative variants?

Question

There are two class features, Perfect Self (PHB p. 79), and Relentless (PHB p.74), which contain the phrase 'when you roll for initiative.' Both allow the character to recover some expendable resources.

When using initiative variants (DMG p. 270-271), what's the best way to interpret this?

As written, these characters would gain their superiority dice much more frequently, or much less, depending on which variant you use. This doesn't feel right to me. Should I read the phrase 'when you roll for initiative' to mean 'when a combat encounter begins'?
What would be the negative consequences of making that substitution?

Answer 1

The feature is based the non-variant rules. In the non-variant rules, initiative is rolled "When combat starts." (basic rules, chapter 9, order of combat, initiative)

If we substitute this timing directly into the features, they clearly mean at the beginning of any combat.

The purpose of the variant initiative rule is to add variety to the combat order. The purpose is not to change the timing of class features. Therefore, the only reasonable way to treat this discrepancy is to leave the features as "at the beginning of each combat."

Answer 2

RAW is a bit out of the window once you introduce DMG variants

Those class features are written based on the normal, default (No DMG rules variants) application of the system. So before I get on to what I think you should do I just want to caution you that resolving this in any balanced manner is going to involve assumed intent for those class features in the normal rules.

I'm assuming the 2 features you are worried about are Initiative Score and Speed Factor and their interaction with the wording you quoted. For the first those features would never trigger and for the second they would trigger every single round if you ran it RAW.

Your substitution should keep the original intent of the class features with either of those rules variants in play

However I don't see any problems with your substitution suggestion as in the normal state of the game the only time you would roll for initiative would be when a combat encounter begins.