I grew up skateboarding an riding bikes. There were always more broken parts, than money to replace them. Me and my friends would come up with ways to "hack" old parts to get us by until we could afford new ones. Sometimes these hacks would become a standard tweak. This behavior has naturally just progressed to a lot aspects of my life.
What got me to start my path to FOSS was two experiences. One was a trying to fix an XP install that had dll that got borked. I used a live cd of Ubuntu to fix XP. When I was doneI repartitioned my HDD and installed Ubuntu alongside XP . How cool was that, quickly Ubuntu became my default OS, there was not some ideological reason for this I just enjoyed using it.
The second thing that happened actually before the OS failure. I thought the idea of downloading music from itunes was great. Until I found out that my music would be locked down. There was no way to access the music with anything but itunes. Or transfer the music to any other player other than a ipod. I decided at that point to only buy the physical cd's and copy it to my computer, unless I could download the music DRM free. I did not buy a digital download from a big seller until Amazon MP3 was opened up. I believe apple has since changed the way itunes manages users music. Of course I am not sure since I have not used itunes since 2006 and never purchased music from them.
As I started using Ubuntu more I was glad I had that internal cringe to itunes early model. I did not have to deal with any DRM encumbered files, I have seen this be a headache for a few friends. The format my music was in, could be played in Ubuntu with no issue. I did have to install a mp3 codec, but; at that time I still had to do that in XP Windows media Player.
There are times when I have to use other than FOSS software. such as the course ware (ALEKS) I am using for school requires Java and will not run using icedtea(the open source implementation of Java). I do keep a VM of XP around for some even rarer occasions.
My move to FOSS software was one of fun and learning. It has been in that spirit I continue to use FOSS. There was a point when, some things were harder for me, each time I pushed through one of these walls it has brought me further into the FOSS world. The eight hours I spent trying to get my ATI card to handle 3D and run beryl was a big one. I really got a kick out of the process and quickly learned the power of the command line. Since then I have setup a home server that has multiple uses. I have learned quite a bit about computers overall. it has even made more knowledgeable about other platforms as well.
This D.I.Y. way informs my life, and FOSS complements those values.