Grumpy reply: the landscape has changed - its the sheer complexity of restoring the original software environment that's the problem.
In terms of Apple, most of my software is now available off the Apple App Store .... so one login later and I can download my software again without even having to fumble around for license keys. Outside of Apple, same goes for my Adobe suite and other vendors.... all I need to do is remember which email address I registered on their site with... the rest does't matter.... forgot password ? reset it ... forgot license key ? its all there under my account.
Maybe Apple make it more seamless ? I upgraded laptops a couple of months ago, and was up and running on my new one within a couple of hours.
Or maybe, as you point out, for me and others with experience, computer migration is at the "piece of cake" end of the spectrum of complexity....
Google et. all will probably tell you the future's in their clouds and you should stick all your stuff on there ASAP.... but with simplicity also comes restricted functionality and security concerns.
You're probably right... if people knew more about the why's and how's there'd be less reluctance in doing things "properly".
Says someone who's just finished watching a 1080p HD film streamed over the internet and delivered over a segregated QoS'd VLAN on a Cisco switch at home... who needs DVDs, Bluray or a smelly Cinema ?
But none of the above would be possible 5 or 10 years ago, its astonishing the pace of change !