Hi Steve, this kind of "barely grazing overlapping surfaces" type stuff can be difficult for the booleans to resolve well.

With this font you get that kind of overlap because of the way the characters stick partially into one another.

Then after doing a flow it means that many of the surfaces involved are not quite 100% equal, they're got just a very slight amount of wiggle between them where they intersect, that makes things especially difficult for the booleans. So yes possibly doing the boolean on the totally straight text initially would have a better chance of success because the overlap in that case would be much more exact with simple planes involved instead of overlapping slightly curved/refit (from the flow) pieces like you have here.

Here's the kind of overlap that becomes difficult, here looking at the underside of the i:






Sometimes that kind of thing can work ok, but it can help a lot the more exactly the surfaces are meeting. When some pieces happen to meet a little less exactly it gets quite difficult for the intersector to get a clean intersection result from all of that skimming overlap.

- Michael