Usually it only takes one time for a new guy to learn to remove the key from a chuck before starting a Drill Press.
On my main drill press, I attached a little cable between the chuck key and the switch safety interlock (little plastic piece). So there's no way I can turn the drill press on with the key in the chuck. This is simple, and gives me a lot of peace of mind.
As far as tightening the chuck, I was taught by the two best machinists I've ever met to "walk the chuck". Tighten one hole, go to the next one and you get another partial turn, and then the 3rd hole, even if you can't tighten the chuck further, tells you that you've done everything right. I very rarely ever spin a bit since I started walking the chuck.

