My saying in regards to learning is "the more you have your line in the water, the greater the chances are you'll get better at fishing". Sooner or later if you're not catching anything, you'll get the help you need. We used to get a kick out of watching guys fish at a local dam, they would walk in and cut in front of the next guys waiting to fish the hole(there was a small slot you could fish and only three guys could fish it at a time, once you hooked a fish you dropped back and a new guy would come into the front of the hole), then they would stand right in the run, which ruined the fishing for everyone else because they could not go up the run
. Then after everyone already told them not to fish there they would cast out into the rocks and get snagged up and loose their rigs, then they would go back into shore and retie and we would start catching fish, until they did it again until all their equipment was gone. What's sad is most everyone there would have not only told them how the system worked(and kinda did when they walked into the run), and would have helped them to get their rigs set up right and even told them where to cast, but they wanted to do things their own way and wouldn't listen.
Much of chain sharpening is the same way, but unfortunately most of us don't have someone right there to teach us, which is the easiest way to learn. The school of hard knocks is, well, hard, but one can still learn if they desire.
I was washing a video last night on throw lines for setting ropes into trees, I thought it was great(enough to make a comment as to such), that there were so many other arborist who've done tree work for many yrs in the comments, that were saying they learned something. I basically commented that it's great to see guys with experience watching a video on something they've done thousands of times with the hopes of learning something new, and they did.
Like my signature says, "If you're not Laughing, Learning, and Loving, you're not Living!".
As far as kickback goes, you just need to watch the top front quadrant of the bar, that's where kickback typically occurs. If you file the rakers down too far that can cause issues with the chain chattering in the cut, and that actually makes them cut much slower, but if you keep control of the tip kickbacks shouldn't be a problem and the next time you file the cutter back that should go away(unless you really get carried away with the rakers).
Risky, you said it again lol.
If you are aware of the causes of kickback, that knowledge along with reduce any risk drastically.
Now, get out and cut, life is risky!