As a long time Apple user, (one could say fanatic) I have just used TimeMachine as a set-it-and-forget-it technology. Buy a big external disk, plug it in, and point TimeMachine at it, and let it do its magic.
Once, I had deleted a file, and I recovered it, pretty painlessly, but apart from that one incident, it has been in the background.
New iMac for Barbara
My wife (the above referenced “Barbara”) keeps her hardware for a long time. Her last computer was a circa 2008 Intel based iMac system. Core2duo, 4gig max ram, and a modest chipset to say the least, but it worked for her for a long time (almost 8 years), but it had been feeling its age.
She finally bit the bullet and we bought her one of the spiffy new retina display iMacs, still the 21″ version (as that is what fits her desk), and it was time to move her files.
The first time ever, I just used the migration tool, plugged in her TimeMachine disk, and told it to go.
About 4 hours later, it was done. I logged in as her account, and BAM, it was just like it was on her old system. Even all the desktop clutter (she likes to capture screen shots of her purchases for later reference).
There were plenty of things not compatible with the new system. Notably, she had an glacial version of AppleWorks (seriously, that was an OS9 product), and a bunch of Carbon library ports from the old MacOS, Pre-OS X, that didn’t work.
Fortunately those were all programs that were no longer needed, or had been long ago replaced (but having software that has been dragged along since the 1990’s should tell you a bit about her longevity of computer systems).
Only two things were needed to be added. First being a new version of Quicken. Easy enough, simple purchase.
The second was a bit tougher, Aperture, which she had switched to when iPhoto died (too many pictures) and preferred to Lightroom, for its kick ass slide show tools. Fortunately, I have a license, and a copy that worked on post Lion OS-X installs. It isn’t going to be updated ever again, but for the foreseeable future, it will be fine.
Time Machine made the migration, specifically for my wife who is quite set in her ways, painless and seamless. I still keep a drive on all my systems with a time machine backup on it, and now trust it a little more having used it.