I was actually pushed in the direction of OpenBSD by the guy who taught me to use Linux, but I stuck to my guns and used Free and it's rather nice. I might try Open this week...
I've had a quick peek at a mates Openbsd box. It all looks very familiar. The main difference being Freebsd has more ports, a greater user base and support ... as well as a cooler mascot
It's similar to ebuild. The ports system is kept simple, in many ways the Gentoo portage is more advanced than BSD ports. In BSD you can't have multiple versions of the same thing, nor is there an equvialent to emerge -p so you won't know in advance what it's going to install. The plus side is it doesn't install recommended packages, it only installs what you ask for (and their dependencies).
Give it some time the number of Gentoo ports will catch up ... ports is definately the way forward, one day it'll all be like that.
I certainly agree that a box is only as secure as you make it but when there is a company involved and what looks (Apologies if you aren't!) a newbie to BSD then having a secure base system is a compelling advantage!
I actually prefer the OpenBSD mascot! Sorry, but I think it's funky!
I've got 3 boxes running FreeBSD and it`s a pleasure to use, the ports collection makes software a dream and the handbook is very helpfull for the more noobish amoung us, right now i have a file server, mail server and and mp3 player/stereo (WIP) machine all running freeBSD, however if your are doing a new install id recomend using either 4.5 or 4.7 and skipping 4.6, it has a couple of irritationg bugs.
As for books on the subject, The Complete FreeBSD is very highly touted, im planning to get a copy meself soo as i have £40 going spare
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