chicken or the egg…?

First, I would do a one up design with the bleed, and with a line showing where you want the die cut to be.

I would then show the design to your chosen die cutting shop (or printer who is going to do the die cutting), and with their input, determine the most economical way to produce the job based on order quantity, your press size, their die cutter size, etc. You can also discuss with them the most economical layout and spacing of the coasters on the sheet.

There is the possibility that, if it is a short run, order quantity might be the determining factor in the number up rather than press or die cutter size.

The die cutting shop will probably want to have the die made, (or at least to specify how the die is to be made), so that they can do the makeready and cutting as fast and economically as possible.

Figure out how the other printer will die-cut. Will die-cut need to run to register?

If die-cutting on a Windmill, you will need a gripper margin and the die margin will have to be tight on the gripper and guide sides—all details that should be designed for in advance and relayed to the die-maker. Nothing less fun than having to saw down a die to make it work on a Windmill. Alternative is to have a bigger press sheet/more waste.l

Care to keep margin for grip is paramount, I have a die maker that wont put cutting rule less than 1/4” from the edge of the wood mount , his argument is sound as the rule exert pressure and while cutting the wood tight to the rule the rulle can break out and the steel contact the saw blade.
I have never had one spring while cutting it downon a circular saw for grip but have a few that have sprung while cutting by hand!!

Thank you for the help!

-sb