"Things that are "broken" that concern me are things like synchronisation between the various device types..."
Interestingly, many years ago, when I first started using a Palm Tungsten device, synchronization with my desktop was truely plug and play- what was on my computer matched what was on my Palm, no matter which device had been updated. True, I was synchronizing a single device with a desktop, but this takes us back to one of the original Unix concepts- a program should do only one thing, but do it very well.
Operating systems, desktops, office suites, synchronizing applications- all are taking the Swiss Army Knife approach- you keep adding more and more "tools", none of which is really optimized for its intended purpose, until one winds up with a totally unwieldy and useless product.
With regards to printing, I have no problem adding new printers to my system using CUPS (drivers are built in to the kernel). I have solved the printer hardware reliability issue by switching from HP printers to Canon printers- Canon gives me 4-5 times the life between equipment failure as the equivalent HP models...