Joe,
Just a few things I did to get over my problems in this area.
I found that when I used to have a morse taper spindle, the tool wouldn't release until the drawbar was given a hefty wack, so there was time to put your hand underneath to catch the falling tool before you hit the drawbar. When I then went over to an R8 drawbar, which released the tool at the slightest whim when the drawbar was loosened, I soon learned to put a large rag under the tool to catch it as it fell. I only lost a couple of 100+ buck carbide tools by them bouncing them off the vice before I learned that trick.
The first thing I bought myself was a cheap ratchet ring spanner, one way to tighten, flip it over to slacken, plus if you forget to take it off after tightening, and start the machine, you will only get a ratchety sound rather than a nasty jam up.
I am lucky in that I have a spindle brake that locks things up when I want to remove the drawbar, if you don't have one, a search on the web will give you some ideas on how to fit a spindle lock to yours, that will leave your third hand free to do whatever you want with.
John