Hi Mike,
my impression now is that chip-out is primarily about avoiding putting stress on short grain sections, and avoiding undercuts. That seems to have mostly to do with sharpness of the blade, order of cuts, and depth of cut.
Yes, you’re on the mark with these thoughts about chip out.
If “with” or “against” the grain has a significant impact on the short grain area, my original question really is why that would be.
If you cut against the grain towards a delicate short grain area, this puts undue stress on the weak area and can lead to chip out. Add a dull knife and undercut and chip out is very likely.
I hope this answers your question. Don’t worry about having it all figured out. The more you chip carve the more it will make sense. When chip out happens you will self-evaluate why it happened and make changes so it doesn’t happen again 🙂
Basswood is a very tight grained wood. Cutting with the grain and against the grain can result in smooth cuts if your knife is sharp. But not all pieces of wood are the same. You’ll find some are more brittle than others. This is when understanding the grain direction is a big plus. And, besides that, it’s helpful to understand carving with the grain as the grain is more pronounced in some pieces than others.