Thanks for the suggestions guys! So, I tried to replace my drill chuck and the problem still continues. I then took my bit out of the chuck and drilled a hole on my press and the bore PERFECT! So this confused me even more. I then checked alignment of the headstock and tailstock one more time and it doesn't seem to meet up as perfect as I thought. This got me to do a little more digging around online and I found this paragraph from Wade's website which describes my exact issue to the T!
"Axial misalignment causes the tip of the bit to “orbit” around the true center line, causing one edge of the drill to cut on the outer face – in turn causing an oversize hole. Generally, what will happen is the entry point of the drill will be oversized, and as the drill progresses into the hole, it slowly starts to be supported by the material causing less run-out, and the bore starts to get smaller and closer to the desired size, but usually it will still be oversized – but tapered – and this will affect how the mandrel holds the blank."
Is there a simple way to troubleshoot this and fix the this alignment issue?
Thanks,
Carlo