There are distributions that work, and work well, right out of the box. I use SUSE Linux daily as my primary (sole except for rebooting into windows to walk users through solutions to their problems) desktop.
It is rock-solid. It never crashes. It comes with a ton of software (multiple office suites, multiple browsers, tons of games, great email applications, and chat programs that talk to EVERY email client out there -check out gaim and kopete). AND it is pretty easy to use and more powerful than any proprietary OS out there.
Maybe it is because I have a few years on you as I have been working in IT since 95, but with a little reading (in the early days), I could get a barebones Slackware system up and running in about an hour. My SUSE install took 30 minutes before I had a login screen and I could do my initial online updates and keep working without having to reboot. That includes installing all the software that I use on a daily basis (office suites, email, chat, etc). Windows, Mac OS, and all of their accompanying apps take hours... and you generally have to reboot when done.
While not all distributions and windowing systems will run on really old hardware, there exist MANY that do. If you have old hardware, run Fluxbox of Xcfe as the window manager and you will go far. You can't do that with Windows.
I don't think you have to go all or nothing. Open Office and Mozilla run on Windows, as do Cygwin, Abiword, the GIMP, and a host of other apps. However, you get the full power of the Open Source design and philosophy running the entire suite of applications and OSes that exist under that mantel.
While it is erroneous for me to say, "Because I could do it, it is not impossible." It is equally erroneous for your failures to forbode doom for others.
Linux/BSD is powerful and increasingly easy to use. Most time invented will pay off. That is a promise that I can make.