In a week-ish, the MetaScript Toolbox will be getting the ability to add tokens to the turn tracker. Actually, the ability is already built and in my test game -- where I was prepping the metascripts to work with the new updates Roll20 is having The Aaron add to script functionality -- but I wanted to release all of those updates together. I'm working on the last of them, now. When that update comes out, you would be able to select the tokens (virtually, perhaps by virtue of a bar value they all have, or something in the token gmnotes that denotes them as part of a group), then iterate over them with a forselected operation and add them to the turn tracker with individual rolls -- which could be rolled individually with Advantage, with Disadvantage, or normally. I'll share the specific and finalized syntax in the release notes for the update when it comes out, but it will basically amount to using a metascript version of the &{tracker} tag. Where, with Roll20 inline rolls, you can use that tag to add or update the initiative value for the selected token: [[ 1d20 &{tracker} ]] ...with metascripts, you can instead use {&tracker} in a deferred inline roll to add/update the initiative value for the selected token: [\][\] 1d20 {&tracker} \]\] Again, this is not functional yet, but would absolutely apply to the situation you describe... and what you describe was one of the usage examples I intended on including in the release notes post I'll put together.
