I am not sure whether I just have bad luck with Emacs extensions. :) I suspect it depends on what languages you're delving into; I found trying to get HTML, CSS, PHP and JavaScript modes all playing nicely together (literally, since the same file could technically have all four, with a secondary template language thrown in for good measure!) challenging. But that particular adventure was a while ago. (My most recent attempt was with Spacemacs, which, uh, I'll just say it has some great color schemes.)
Re: Emacs Lisp: well, I did say "often feels like," not "actually is." :) I'm sure you're right; it's just that sense that a lot of early problems get solved by "to do the thing you want to do, paste this code into your init file," and getting past the feeling that you're assembling a configuration you don't reallllllly understand -- and thus may not be able to debug if something goes wrong -- can be a hurdle.
I don't doubt vim is very powerful for things like programming, but can I use it to automatically scan my emails for keywords and make TODOs out of them (in just a few lines of code)? Can I use vim to compute derivatives of math functions and automatically insert them into LaTeX documents? And so on.
Don't look at Emacs merely as a programming editor. It's a playground for anything textual.
It's probably not hard for someone to do that with Emacs - all the bits and pieces are there. I wouldn't be opposed to this.
> They're both difficult for beginners to get used to, but once you get over the initial learning hump, Vim was always much easier for me to tweak and configure.
At the risk of starting a pointless war, I suspect it may be because Vim just has an order of magnitude fewer features than Emacs does. Many people have wanted Org mode in Vim, and no one has been able to make a good one.
> when it comes to not stomping on one another. Every attempt I've made at getting serious with Emacs has ended in spending hours trying to get two or three extensions I want to use to play nicely with each other
I believe you because this complaint does come up from time to time. I must have been simply lucky that this has been a very rare problem for me. In fact, I often tell people Emacs is great because one can take disparate packages and use them together to get powerful features. To me it exemplifies the UNIX philosophy of combining tools better than most UNIX utilities themselves do. The worst I've encountered is a conflicting keybinding.
> you can do almost anything with it if you learn Emacs Lisp, but it often feels like you must learn Emacs Lisp to do almost anything with it.
I view that as one of the biggest myths. I was a power user for about a decade before I learned to even write a loop in Emacs lisp. The most I knew was setting the value of variables. That's enough to be a power user.
Now that I know Emacs lisp, I don't have a burst of productivity compared to when I was ignorant. I've customized to solve a few annoying problems, but I've not had any moments of "Oh man, I wish I knew how to do this all these years."
I don't encourage Emacs users to learn elisp. If I ranked things they should explore in Emacs, there would be a lot of stuff higher on that list than learning elisp (org-mode, etc).