1. avoid bobcad/cam, their software is ok but the salesfolks will hound you to death to buy more.
Cambam, Meshcam, Dolphin Partmaster, Vectric are all quite good and won't break the bank,
try them first and see what works for you.
2. If you have them, might as well give them a try.
3.glacern are nice looking and you're sure they are quality, the grizzly may be good
but may be off a couple thou here or there.
4.The collets have some give but if you only plan to use metric tooling go with metric collets,
ER collets are more common.