IMHO, Evil Mode makes to use emacs doable OTOH, the fact that there are so much extensions and possibilities under the hood makes to use emacs mandatory! :P
1) intial emacs setup: it feels really tricky to just get basic editor sanity configured (auto-indent, syntax highlighting, etc.)
2) I worry that by using evil mode, I lose out on a lot of the goodness of emacs major and minor mode's. Do you remap everything to be more vi-ish for each mode that you use? I guess that is fine but the transition just seems daunting.
I haven't seen any lost functionality by using evil; modes that define bindings continue to work, and the usual C-x/C-c/M-x/whatever works fine with evil. There is the odd major mode that doesn't work with evil out of the box (usually if it redefines j/k) but most have no problems. You can still use most (all?) regular Emacs movement commands with evil as well.
I'm still trying to figure out the emacs portions of emacs. I don't have the work flow quite right; things like buffer management, saving sessions, shell in emacs, etc.
1.http://www.emacswiki.org/emacs/InteractivelyDoThings
2. http://www.emacswiki.org/emacs/DeskTop
3. For 3 I just use built in shell-mode, but what is really neat is saving your shell session to a file "C-x C-w" every so often. Then if you reboot or crash or whatever, emacs-desktop will bring back all your open files and all your shells. I usually have 3, regular bash, a sql session, and maybe an ssh session to somewhere, all with a full record of what I've done, sometimes going back months.