I'm trying to model this kind of stamping tool. The Wrap-feature will do a quick and dirty version, but what it lacks is a Draft on the straight sides of letters.

A workaround I came up with is to do a reqular "Extrude Boss/Base" with "Draft" enabled on a planar surface that corresponds to "unwraped" curved face and then Deform those individual solid bodies on to the curved face.

Problem with this is that if (and when) I need to change the text the Deform will fail as it won't allow me to select the whole "Boss-Extrude3" as a "Bodies to be deformed".

Any ideas how else I could accomplish the same so that I would be able to change the text and wouldn't need to pick out the separate bodies one by one?