Because of the length of this post, it is in 3 parts
Part 1
This is a hard one to answer because each has features that make them somewhat different and easier to learn and use, or not.
For the record, I can only speak to PSREdit and Win500. These were the two I evaluated for my needs because I found the Butel ARC software difficult to find for a trial in my timeframe compared to those two I did test.
Anyway, PSREdit preformed very well, was pretty intuitive and had a decent help file in it. That help file made it quite a bit faster to learn. It had good functionality across the board and I was able to upload to it, make substantial changes to my channels, and download back to the scanner pretty quickly. Any questions I encountered were usually answered in the help files.