Short bio: Computer Scientist, FOSS supporter (read more)
Tux Machines (TM)-specific
For a Linux distribution that focuses on user friendliness, it does surprise me that Linux Mint offers no seamless upgrade path. In fact, the underlying philosophy is that upgrading an operating system is a risky business. However, I have been doing in-situ upgrades for both Ubuntu and Fedora for a few years without any real calamities. A mishap with a hard drive that resulted in lost data in the days when I mainly was a Windows user places this into sharp relief. These days, I am far more careful but thought nothing of sticking a Fedora DVD into a drive to move my Fedora machine from 14 to 15 recently. Apart from a few rough edges and the need to get used to GNOME 3 together with making a better fit for me, there was no problem to report. The same sort of outcome used to apply to those online Ubuntu upgrades that I was accustomed to doing.
The recommended approach for Linux Mint is to backup your package lists and your data before the upgrade. Doing the former is a boon because it automates adding the extras that a standard CD or DVD installation doesn’t do. While I did do a little backing up of data, it wasn’t total because I know how to identify my drives and take my time over things. Apache settings and the contents of MySQL databases were my main concern because of where these are stored.