You asked about workflows needing offset of offset...
here are a few:
Any place you are building mateing assemblies with clearance one would likely do an offset for thickness then another offset for clearance
on the mating part....
This would also apply do things like electrical PCB outlines, ie I have a spot in my machine to put the electronics...
I'll offset the area to make wall thickness for the cavity, then I'll offset the inner wall to allow tolerance build up and then
export this inner twice offset outline as the potential PCB outline to give the Electronics/PCB guy.
Any structure that will have internal flow channels such as cooling for molds etc...
would benifit from having offsets of offsets....
You can see the internals of a part I built that has offset of offset of offset...
(Done in Rhino, tryign to recreate in fusion but its takign a bit...)
http://unreasonablerocket.blogspot.com/2015/11/motor-design.html
Another use case is where you have clearance issues, ie I'm making a turned surface with clearance and oring seals...
There will be the outline, the offset for thickness, the offset for clearnace, then the offset for oring depth...
One might choose to dimension each of these seperately, but I can also see using multiple offsets for at least some of these....
Another multiple offset use might be a recesed bolt hole...
I have the thread diameter, the bolt clearance diameter, the bolt head clearance diameter and the tool (socket) clearance diameter.
One might do these as individually dimensioned circles, but I could easily see this as offsets wherr one ended up with a complex recess geometry as the rsult of multiple nearby bolts.
In general one can work around this by having multiple offsets from one core line, but asking the designer to do math to calculate offsets if fraught with peril.
IE the prototype is built, there is not enough clearance so the designer goes back in a ads 0.5mm to the clearance. If the clerance is defined as the differnce between multiple individual offsets, its not going to be obvious to the designer which dimensions to modify, and if he has to modify more than one....