How would I go about adding in a .25" bleed on the shape attached? The magenta line is the final shape. These will be diecut so I'm hoping it won't matter too much but I'm struggling to figure out the best way to extend the shape. The top and bottom edge are simple but where the rectangular shape meets the circle, things get awkward. What am I not thinking of?
Bleeds do not have to follow shapes exactly. They simply need to be a minimum distance from the artwork.
Factor .25" outside the circle and then run the bleed as a rectangle to that distance. It will be greater in the area of the vertical strip, but that won't matter.
In this case, just extend the strip edges making certain the circle cuts into the strip properly. Since the circle isn't printing, you merely need to ensure the curved edges around it are correct for the bleed.
I would probably consult the print house with the 3 options above and ask them which one they feel is best suited to meet the bleed requirements for their die cutter. without consultation, I'd run with the rightmost option (that shows the cursor on it).
The primary issue is, you have to imagine a hairline variance. So, if there is a variance, which would you prefer... a little curved white cutting into the strip, or a little blue cutting into the circle? I feel the right option eliminates these factors as much as possible should there be a variance.
Select the outside path and choose Object > Path > Offset Path and experiment with the setting. It will give you a replica of the path that will allow you to hold bleeds.