I think it would really help you to have a play with command line Git, just to get a feel for what's going on. SSH keys aren't hard to learn and are useful enough to be worth the time spent.
It's not about being unfamiliar with the CLI, it's that Windows isn't like OSX/Linux in that you can just store your keys in a .ssh folder and be done with it (at least not if you don't use cygwin/msys)
The method I chose in Windows was to use pageant (part of Putty) to load the keys. Not sure if I missed this option but you can't autoload keys so when you restart pageant you have to readd the keys (which is not terrible bad, just annoying).
Haven't tried Github For Windows yet but if it fixes the hassle of using ssh keys then I'll probably use it as my main git client for Windows.
It's not simply a matter of checking an option unfortunately, but you can still get Pageant to load keys at startup by creating a shortcut to it in Programs -> Startup:
You can autoload keys with pageant. You have to change the shortcut in your Programs\Startup folder that loads pageant itself. From memory I think it's as simple as adding the paths (in quotes) space separated after the executable. It's certainly in the help documentation at any rate.
> Windows isn't like OSX/Linux in that you can just store your keys in a .ssh folder and be done with it (at least not if you don't use cygwin/msys)
Then, by all means, use Cygwin or anything that helps you, even if it doesn't come with Windows, if it isn't provided by Microsoft, doesn't look familiar and if it doesn't play well with Visual Studio. If you code for Windows you are coding against an insanely complicated set of APIs.
It's not a question of familiarity, it's that git doesn't play nice on Windows. It requires a POSIX emulation environment, like cygwin, which is a second class experience.
Compare this with Mercurial, which runs great from the command line on multiple platforms. I actually prefer the command line for SCM work, but git makes it hard.
Putting all of your SSH keys in a .SSH folder (inside your user directory) and setting up OpenSSH to look through those when you try to connect to something is exactly what installing Git on Windows does.
This seems pretty friendly to me. Is there something I'm missing?
By all means switch to using the GUI after.