Well, I am trying to approach this a number of ways so you can understand my madness. Choosing a Linux distro is not that difficult. Let's start off with what a users sees, the GUI. The GUI is the face of any operating system, The GUI affords you an easy way to work the guts of the operating system to do what you want. There are as I said 3 main desktops, KDE and Gnome are the most well known, KDE seems the most like MS Windows but Gnome is not that different. Then there is Xfce which is a little leaner at resource use. Which means that Xfce will work better on a less endowed computer. Then also there are what is known as window managers, which are less integrated than full desktops but still sufficient to get at your system. The thing you need to know is that it is all point and click. Some window managers are Fluxbox, Ice, Enlightenment. I will say this to those who think Linux is hard to use, or for geeks. The command line or terminal window is available when and if you need it, but the same is true in MS Windows. The fear is in not knowing what to expect when you hit the return. This is why user forums exist to tell you what to do and expect so you are not in the dark.
The next thing to be concerned with is the application package management system. There are three, RPM, DEB and TARGZ. You ask which is the easiest/best to work with? I say DEB is the best, then RPM, then TARGZ. That is my opinion, different distros have tools to make working with files a breeze, your likes might be different. Distros are classed by these package management systems. Red Hat and Red Hat based distros use RPM. Debian and Debian based distros use DEB. Slackware and Slackware based distros use TARGZ. Now add on the GUI of your preference and you can begin to see why so many distros.
The third consideration is system administration tools. Are the system admin tools in one place or scattered? How are the desktop configuration tools, the disk management tools, network tools and especially the installation tools. If you are using the live-CD, is it easy to save your files and settings?
The last thing to know about is how to get your Linux driven computer to mesh with the MS Windows dominated world. How to get MS TT core fonts so that your docs will be compatible. How to install codecs if you need them for multimedia. How to add extensions to web browsers like Flash. Then how to deal with 32 bit extensions when you have a 64 bit programs, if you need to. Finally, how to install video drivers, install printers and deal with WiFi.
There is a lot of plug-n-play but some hardware needs serious tweaking. You need to check the user forums to see how others have dealt with those problems. Once you have entered into the Linux world it can be consuming but no worse and for some much better that dealing with MS Windows. I hope your Linux adventure is a long and interesting one. Breaking free from well honed user habits takes a little struggle and looking into a few things clears up a lot.