I'm making a simple little low table/bench for my deck, and I'm trying to
toe screw the 2x4 side rails to very heavy 4x4 legs (just leftover cedar
from my deck....I wanted a "heavy" look). I'm toe screwing from the inside
to hopefully hide the screws entirely.

To position and countersink the screws I've been (starting with a wide bit)
drilling at 90 degrees for a quick 1/4" depth to give me a place to hold the
bit, and then redrilling that hole at 45 degrees for another quick 1/4" to
make a 45 degree hole ready for the smaller bore drilling and then the
screw.

It always seems that this is a harsh way to treat the wood....no matter how
careful I am, the bit at 45 degrees likes to much up the grain. Now this is
hidden anyway, but...is there another way to "seat" a 45 degree toe screw?

Jeepers I hope I explained this well enough.