Since changing jobs I now mostly work with Unix machines rather than Windows ones. Mostly it's a not too unpleasant experience (once things are set up the way I like them) - Unix seems to be much more flexible and configurable than Windows, even if some things don't work quite so well out of the box.
One area I have run into difficulties with is editing text files. When I first started using DOS I used to use edlin, which is horrible. After a while I discovered QEdit on a magazine cover disk and loved it - very quick to load and scroll (even on an 8MHz 8086 machine), easy to use but with powerful macro facilities there when you need them.
I used that up until 2002 when I switched from using Windows 98 to Windows XP and QEdit stopped working so well. I bought TSE (the updated, renamed QEdit) and it was worth every penny - everything that was great about QEdit was the same or better in TSE and I've used it almost every day since for almost every text editing task (though I have been known to use the Visual Studio editor occasionally for its Intellisense goodness). Moving from QEdit to TSE I discovered that the Windows shortcuts for select, copy and paste (shift+navigation to select, Ctrl-X to cut, Ctrl-C to copy and Ctrl-V to paste) were much quicker and easier than the QEdit defaults (which I think originated in WordStar) Ctrl-K B, Ctrl-K K etc.
When I switched to Linux, TSE was one thing that I missed most. It works under Wine but not particularly well (it always defaults to full screen, copy/paste integration doesn't work and scrolling is painfully slow). A Linux version of TSE is in the works but doesn't show any sign of materializing soon.
Joe is the closest thing to TSE that Linux has to offer but it's a bit limited and just different enough to be annoying. It also isn't available on all of the machines that I need to use. The latter requirement basically means I have to make the big choice - vi or emacs?
I gravitated towards vi initially as it seemed to be a bit more lightweight and I had some experience with it from my brief stint using Debian sometime around 1999-2000. I relearnt how to do the basics, put it into syntax highlighting mode and fix the colours (dark blue on black is unreadable to me, and of course comments have to be in green). But it still drives me crazy - I never know which mode I'm so I'm always inserting ":q" into files or (worse) typing text which gets interpreted as random commands and then trying to figure out what I did and how to undo it.
I eventually found out that most people who develop GNU software use Emacs (I saw a lot of people using it at the GCC Summit) and that it has great features for writing C code according to the GNU guidelines. So I decided I had better learn Emacs. I had used it a bit at university (the Physics department gave us a brief tutorial in it as part of the Fortran course). I have also learnt a bit of Lisp in the intervening years and having Lisp as the macro language of an editor seemed to be a rather reasonable thing to do.
One big problem annoyance with all the Unix editors is that none of them support the Windows-style shortcuts I mentioned above (plus Ctrl-Z, Ctrl-Y, Ctrl-A and Ctrl-S for undo, redo, select-all and save) by default. I almost squealed with delight when I discovered the CUA mode in Emacs 22 which brings it significantly closer to being the perfect editor (at least once I figured out how to tweak various terminal settings to actually make it work - this helped. Unfortunately many of the machines at work still use Emacs 21, so there was some more fiddling required to install the CUA package.
Then I need to figure out if I can get the scrolling behavior to work like QEdit's, fix up some behaviors related to tabs and (once again) fix the syntax highlighting colours. "Eventually I'll have everything the way I like it" may be the mantra of a great many Linux users...
Part of the reason this is so difficult is that customizing editors is generally considered an advanced thing to do - you really have to learn the basics first. But if the first thing you want to do with a new editor is make it act like your old one, you first have to learn the default way of doing things, then do the customization, then unlearn the default way of doing things. My natural inclination is to take shortcuts - try to figure out the advanced stuff without really getting the hang of the basics first. This does seem to have a tendency to complicate things.