I haven't loaded up the files to check but my guess is that you are starting the feed in move too close to what you want to cut (not enough distance to establish the compensation offset). Just looking at the code it looks like your feed-in starting point is only 0.300 from your first cut line, so maybe a 0.375 diameter tool didn't have enough room to establish the compensation but a 0.234 diameter tool did.
The docs recommend a two move sequence for entry. Then the first move usually seems to get the tool moved to the compensation offset and the second one actually enters the cut pattern. I have had best luck when the first move was a G01 whose length was at least the radius of the cutter. If I am entering on a straight side I circle in G02 or G03 depending. If I am entering at a corner the second move is directly in line with the side I am going to cut. (Hope this is clearer than mud.) If you need I can post a cutter comp file that works to illustrate.