Rolling Initiative

So, I have multiple enemies, but since they are the same enemies, I'm using one sheet for multiple tokens. Is there a way to roll initiative for every token on the objects and tokens layer? And will it read tokens that share the same sheet as separate entities or one single entity?

The only way to roll for multiple tokens at the same time is to use the API (Pro subscriber perk). There's a specific API called "Group Initiative" that does this well, and I believe other scripts like Combat Master can also do it.

If you look up the initative roll buttons name, you could make an %{selected|INIT} macro button that you'd click and then select token to roll initative, and then repeat the process for each enemy token. It should be a bit quicker than having to open the sheets of each character and then do the selecting with the rolls. What sheet are you using in your game? %{selected|INIT} should work for D&D 5E by Roll20, but other sheets don't have the exactly same name for the initiative button.