I had recently gotten a larger hard drive. I installed Photoshop and Lightroom and got them configured. The drive failed, and I got a replacement drive. I had to install my applications again and configure them a second time. Because I have been thinking about and writing down the things you do to configure Photoshop and Bridge for future tips, I didn't have to test settings and try to remember what I did. I didn't even have to look at the tips I'd written. I knew what I wanted to do.
The more you know about a difficult, complex application, the less stress you have when working with it.
And no, I didn't lose any data at all when the drive failed. It failed slowly, I spotted symptoms, and identified that it was a failing drive. I was able to ensure that all of my more recent changes were captured in convenient locations and I lost no data at all.