If updates are giving you problems, I'd suggest you look to your hardware, I've been using the system I'm on now, for the last 7 releases, and I'm currently running the Saucy development version, in those three years, I've only had three occasions where my system had a problem, two of the problems were to do with graphics drivers, and the 3.7 series of kernels wouldn't boot at all on some AMD cpus.
My systems isn't, and wasn't high end when I put it together, put for me, MSI motherboards, AMD cpus and Nvidia graphics adapters seem to be a great mix for a reliable system.
"Everybody is ignorant, only on different subjects." Will Rogers
Op, i've had similar problems. I use windows 7 primarily and it works great! I use ubuntu server in a virtualbox for when i feel like messing around. Ive previously asked here for a definitive list of supported hardware and apparently ubuntu runs great on everything so...we get what we pay for. Ubuntu server has been handy. I like using it but if you really want to use it you must be willing to learn.
Windows is fairly easy for me to navigate. But that's only because of the household DOS and Windows 3.1 computers that I grew up using, and then sticking with Windows through Windows 7. That's a lot of time to devote towards operating system use on a daily basis compared to my month of Ubuntu use.
Ubuntu when I first came over was overwhelming. Windows was, too. I don't mind learning the ins-and-outs of Ubuntu because I understand the learning curve is there. I actually enjoy computing and learning.
However, it's hard to ever consider Ubuntu being a mainstream threat when most mainstream Windows users have never even seen or used command prompt, but daily user activities on Ubuntu require terminal for the most basic actions. I know that since I originally tried Ubuntu some years ago to the point of 13.04 there have been many, many GUI additions to reduce terminal use. However, it's unavoidable with the current hardware support for Ubuntu.
Even on an installation that went flawlessly with no driver or hardware issues, configuring the experience is still too much of a task for most casual computer users.