Well, you probably know the online documentation is vast. I think the trick is finding what not to read.*
Have you commenced choosing a distribution? It seems you already have some ideas about what you want to get from it. There are some desktop distributions which are not bad at providing an eased introduction, but I suspect you may be better off just jumping in the deep end. If it is for a work project, it may be worth considering commercial support for the first year.
I used
documentation by Machtelt Garrels when getting started. His writing is very easy to take. I think his guides are best used at a terminal, to try things out (typically with BASH). You may like to install a distribution to play with, and take another look at what's available after learning a bit.
Have a look at
The Linux Documentation Project. I think I read Binh Nguyen's
Linux Filesystem Hierarchy guide from there, and referred to his
Linux Dictionary as well.
I have found Linux distributions very good for my daily computing, and for software development. BASH is also my favourite shell. I prefer Windows for multimedia and music tasks though. Should be good for your server application, though I haven't had to settup a server for anything I am directly involved in.
Another thing worth thinking about is hardware support. Have you already got your server hardware? Does it require any exotic or unusual peripherals? If so, check which products have good Linux drivers. Linux has come a long way with driver support, but it is still an issue sometimes. I think most servers would be pretty bare bones with peripherals though, so you should be fine.
Linux can be frustrating sometimes, but usually in ways different from other OS's, so a bit of persaverance, and lots of reading is in order.I generally haven't found users in Linux fora to be vey responsive to help requests. That me because I was having uncommon issues though. Many of the common questions will be answered in several places already.
Good luck!
* Somtimes one can go down a long path of fault finding or information gathering, just to find that all your efforts are completely innappropriate to your distribution.
edit - added clarification footnote