Perhaps the problem is you are TOO familiar with other programming methods. I am a novice to CHIRP; I read the programming info & the detailed field definitions and was merrily up and programming in a few minutes. There were a few minor hiccups understanding some of the idiosyncrasies of the system but nothing of any significance. I was quite happy with the learning experience and didn't find programming in CHIRP difficult at all.
I noted a similar experience in driving automobiles. When driving a new car for the first time, I find I am much more successful if I shift using the shift pattern of the new car, rather than the shift pattern of my old car.
Lee N8VYH