Hi mdesign, I think you're probably running into some of the same stuff we discussed previously here:
http://moi3d.com/forum/index.php?webtag=MOI&msg=9541.4
I would think you should be able to boolean stuff with tightly bent corners like that but it's pretty unlikely that calculations involving surface offsets (which includes filleting) is going to be able to cross over such tight bends in small concentrated areas like your geometry has.
That's more related to those kinds of shapes being difficult to process, not exactly whether it was created in sub-d and converted to NURBS or modeled in NURBS initially.
If you built something with those kinds of tight bends in it directly in NURBS you'd see the same kind of problems.
Typically in CAD those smallest tightest fillets are added in at the end, you usually don't want to have them baked into your geometry already and then try to do filleting or shelling on top of those.
- Michael
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