I think the problem is that there is an expectation that you'll have a fairly strong background in this stuff before you start using it. But that's not the typical user that we attract. We seem to attract almost entirely Windows-only users that have never used anything else and think they'll just "pick it up" as they go.
Then they get pwned right off the bat since even the hardware you should be running isn't your typical windows hardware and they blow a fuse.
Then instead of taking a few months to get familiar with an OS they've never touched before and without considering that the manual might be helpful, that there might be stickies in the forum to help you get a lot of things right, or that they really should learn some of this stuff, they show up and start posting. After plowing through it like a semi and hitting every stop sign they could(since they ignored the resource we've already provided) they feel accomplished.
Then they touch the jails.. and the jails touch back... violently.
I'm not exactly a FreeBSD wizard(I got pwned last night trying to setup a new linux jail with the 9.2.0-RC) but I setup the Owncloud plugin in less than an hour without having to Google anything. It's been flawless for me to use too.
As soon as 9.2.0 comes out I'm going to do some more plugins I think.
Overall, I think the problem is people get too cocky with learning a new OS. I don't care how you justify it to yourself, but you just aren't going to learn FreeBSD in a few weeks. PERIOD. You didn't learn Windows in a few weeks, did you? Why would you even entertain the notion you could learn a FAR more sophisticated OS than Windows in a shorter time?
People just don't do the proper research and when the get pwned the immediately assume that they couldn't have done anything wrong and that it must therefore be FreeNAS or the plugin that is junk. I bet if I installed every plugin offered in the appcafe I could have them all up and running in a weekend with no Googling.
It's all about your knowledge and not about your ability to plow through everything like a mack truck. When the weather gets really bad those mack trucks end up on the side of the road too!