Sorry don't know about the software problem but as for the engraving I might be able to help. When desinging the part did you run a simulation to see if the cutter was cutting all the sections? I just did some text for a part I was making and I know nothing about envgraving nor do I have an engraving bit so I made the letters as big as I could while still being able to have a 1/4" endmill fit inside the lines. When I had the text smaller certain parts of the lettering were not getting cut because the cutter would not fit inbetween the lines. What I think is happening is the bit you're using won't fit within the size of the lettering you have desinged so the program only tries to mill out where the cutter will fit into. Right now I dealing with the same thing how to do small text without having to use a ton of specialized bits.