Hi Seb, I can't seem to connect to any of those picture links, I get an error: "Sorry, that page was not found." for each link.

MoI does not have any mechanism in it to automatically find the widest possible radius for filleting, so it would not really help you for automating that particular thing really.

Actually one of the features of MoI's filleting mechanism is that it tries to allow fillets of actually greater than just the tightest radius bend in the edges and will try to put in a separate kind of blend in those places, like this:

Here's a shape with a tight bend in it:



A regular fillet can go up to about this radius here before the fillet will start to cross over itself:




But MoI's filleter will actually allow you to go to a higher radius than that, it will break the fillet into pieces that stop before running into that tighter bend and put in a separate kind of blend in that spot:



So because of that the max radius for this particular shape is something like this:




So I'm not quite sure what you are looking for by "maximum radius" exactly - do you mean something like this here where the fillet may be eating away a big part of the object or do you mean the maximum radius before the fillet would have to start being broken up into several pieces like shown here?

It could be possible that MoI could be useful to you, but MoI's filleter can also be sensitive to a lot of things as well and it's not unusual for font shapes imported from illustrator to have a lot of things that are pretty difficult to fillet in them, things like excessive segmentation and pieces not meeting completely smoothly and stuff like that - MoI's filleter will have difficulty with those kinds of things too.

- Michael