For what it's worth, I have done the upgrade route. It took a long time, but I didn't lose any data in the process. The trickiest thing is that you do have to tackle any hardware incompatibilities that might have plagued each release. With 9.10 in particular I had major video problems that would black out my screen--making solving the problem pretty tricky! So in theory upgrading through several releases does work without data loss, but in practice it can be a real hassle.
You can do a fresh install, though, without backing up to a separate hard drive (or losing your data) if you set up a separate partition on your hard drive for your /home folder. Then just do a fresh install of the operating system and choose the main partition for the OS installation during the setup process. Either during setup or afterward (using Gparted) you can mount the partition with all of your user data to the /user location again and you're ready to go. If you Google it there are quite a few good articles that walk you through the process.
Of course, the actual software still needs to be installed again, even with a separate /home partition. But the trade-off is that your OS partition can be set up using a newer file system like ext-4 that will give you better performance. If you do have to re-install your applications, the new software centre makes it pretty easy and quick. Also, I'd recommend installing Ubuntu Tweak early in the process, since it gives you a nice quick interface for setting up common outside repositories (like medibuntu or the mozilla repos) that would otherwise involve some surfing around to find the ppa addresses.