Better now that it was a couple of years back (I still use Windows at work) but still some way to go.
It's a point of pride to me that my Win7 box at work is so slick and well-tuned, compared to other peoples' Windows machines. But for the life of me I can't make my MacBook look any better than my Mom's. Nothing makes me happier than being able to be brutally effective on my cool-looking Ubuntu box at home that uses customized window managers and a dozen productivity hacks. But you don't even have to be nerdy to use a Mac well. Where's the fun in that?
This comment is only half tongue-in-cheek.
But as I got older and my free time shrank it just felt like an overhead and time I'd rather spend doing other stuff.
I also prefer built-in software to 3rd-party alternatives – Safari over Chrome/FF, Terminal over iTerm, Spotlight over Quicksilver, etc. It took a while to adopt Apple's way of thinking, but it has made my life easier in the long run and saved tons of time to do more important things (eg. spend time with my kid^H^H^H^H^H^HHacker News).
nocturne - invert or dim the screen, helps your eyes stay relaxed in different lighting situations: http://http://code.google.com/p/blacktree-nocturne/
divvy - quick window management, surprisingly handy, spaces becomes more useful with this as well: http://www.mizage.com/divvy/
visor - system-wide terminal via a hotkey: http://visor.binaryage.com/