A few years ago, a new tool was added to Calypso, called Caliper Distance. This characteristic makes it easier to measure min/max distances between circles, as shown below.
In the past, you would have to create theoretical features and intersections first. The Caliper Distance also has the flexibility to report average/min/max distances from other features, such as planes and cylinders.
Look for Caliper Distance under the menu: Size - Distance - Caliper Distance.
The "determined from..." option allows you to report distances from the calculated geometry (CAD Entities), or from the true min/max points (Measuring Points). The Measuring Points option is useful when you need a direct physical comparison to a caliper measurement, including any form deviation on the surface.