I think that something has to be said for to what you are accustomed. For example, I grew up using BSD, because my father was an electrical engineer and wanted me to know "what the real men used" as he put it. So, I learned BSD, Solaris, and AIX which are the systems used at his work. Coming to GNU/Linux, I found Slackware to be easiest for me. My ex-wife's mother worked at AT&T when she was younger, and as she was coming to GNU/Linux she asked for something similar to the UNIX she had used. I showed her Slackware, Arch, and Gentoo. She thought all three were amazing and chose to go with Gentoo. She thought the source based 'emerge' was the coolest thing ever...
I never would have switched to GNU/Linux had BSD had as good hardware support, and as large a community. That said, I think that GNU proper is even worse off. Of all the Unices currently available, GNU/Linux is the only one that seems modern enough and popular enough to stand against OSX and Windows as a real competitor in the business world, desktop market, and in the end on my personal machines.
The different flavors are no more or less hard than one another in all truth. If you want easy to use Slackware, you always have Slax. If you want easy to use Debian you have Ubuntu. If you want easy to use Gentoo you have Sabayon. Any distribution can be made to be nearly exactly the same as another distribution, you simply must be willing to put in the time and effort required. Personally, I love Slackware and GoboLinux. That's about it. Most other distributions just frustrate me to a point that is totally out-rageous.