For my 20th level rogue/fighter I had enough that I could roll once. So 2 D20s (in case of advantage/disadvantage) plus D8s, an extra die or two (custom weapons that did extra damage) per hit plus sneak attack dice.
The trick to keeping track was that I use a clear plastic sheet protector for my character sheet that I recorded AC hit on one row and damage on the next for each color. Some dice (green in sparkly) were if I was action surging, and I'd record crits with a "C" So I had something like:
[table="width: 500, class: grid, align: center"]
[tr]
[td]Sneak[/td]
[td]Black[/td]
[td]Blue[/td]
[td]White[/td]
[td]Green[/td]
[td]Sparkle[/td]
[/tr]
[tr]
[td][/td]
[td]16[/td]
[td]23[/td]
[td]C[/td]
[td][/td]
[td][/td]
[/tr]
[tr]
[td]24[/td]
[td]20[/td]
[td]21[/td]
[td]30[/td]
[td][/td]
[td][/td]
[/tr]
[/table]
But that wasn't the worst, I've done this for a long time and had a 3.5 character (with animal) that needed close to 60 dice when he was retired. I roll/add while everybody else is taking their turn so my turn takes less than a minute. Does a 16 hit? No? What about a 23? Ok I do ____ damage.
So yes, I have a really big dice bag. Something like

The trick to keeping track was that I use a clear plastic sheet protector for my character sheet that I recorded AC hit on one row and damage on the next for each color. Some dice (green in sparkly) were if I was action surging, and I'd record crits with a "C" So I had something like:
[table="width: 500, class: grid, align: center"]
[tr]
[td]Sneak[/td]
[td]Black[/td]
[td]Blue[/td]
[td]White[/td]
[td]Green[/td]
[td]Sparkle[/td]
[/tr]
[tr]
[td][/td]
[td]16[/td]
[td]23[/td]
[td]C[/td]
[td][/td]
[td][/td]
[/tr]
[tr]
[td]24[/td]
[td]20[/td]
[td]21[/td]
[td]30[/td]
[td][/td]
[td][/td]
[/tr]
[/table]
But that wasn't the worst, I've done this for a long time and had a 3.5 character (with animal) that needed close to 60 dice when he was retired. I roll/add while everybody else is taking their turn so my turn takes less than a minute. Does a 16 hit? No? What about a 23? Ok I do ____ damage.
So yes, I have a really big dice bag. Something like
