Great question and great answers. Having been a woodworker for too many years I can tell instantly when a tool is dull just by how it is interacting with the material, what the machine is doing, and what the cut looks like. I usually notice the first two and then confirm with an inspection of the cut. I think that all of us rookies need to put some chips under our belt and experience will be our teacher. A retired machinist gave me a bunch of used tooling some of it actually no good and told me to try them all out on scrap to see what the results were. It has been a great learning experience for me. I can see what a chipped mill does vs. a dull mill vs. a bent mill... I spent most of one day trying them out at different speeds and feeds and materials. When I took out a new high dollar 1/2" 4 flute to try on some steel is was amazing to feel the difference. Looking at your cuts under magnification is also a good experience.
I spend a great deal of time at least skimming posts here as you never know what little tip one of the experienced guys will mention, or a short story. This is an awesome group that has thought me so much as I dive into the world of metal.