BigDaddyO,
First let me clarify that I am no leather working expert. I have only been stitching leather since September, so please do not take my word as the gospel. I have used awls with four different shapes – round, diamond, rectangular, and convexed on two ends like an eye.
In my limited experience, I find the circular shape to be the easiest to use for most applications, as I must only focus on placing the point in the correct spot and driving it straight through the leather. The other shapes have less symmetry and thus require you to align the awl on two planes rather than one and then drive it through straight.
I believe the diamond and eye-shaped awls allow the thread to better stack which allows for a cleaner looking stitch if everything else is done right. I have a 6 hole punch shaped like a stubby fork with diamond shaped tines. These tines are aligned through their mid points, but they are canted about 30 degrees from the plane defined by their centers of gravity. This orientation further enhances the thread stacking effect and limits the potential for errors in alignment. The look of this arrangement is very clean, but it has a staggered appearance similar to this /////////////////////// rather than the effect I get with the circular awl which looks more like this ------------------.
If I am incorrect in any or all of my assumptions, I hope one of the more experienced leather workers will make corrections.
Take care,
Malcolm