Making ssh easier for our Windows user community

I would suggest using Cygwin and installing SSH through that. Then you can setup ssh-agent and even configure it automatically with shell scripts. That way, you get to use SSH almost as if you were using it on Linux instead of using PuTTY or msysgit. Plus, you get the benefit of being able to automate things with shell scripts and Cygwin. Here is just one of the many different ssh-agent scripts I found to get it working with Cygwin. Also, I find Cygwin's setup and installation very flexible. Since it just downloads files from a mirror and puts it in the root of your C: drive, I'm almost positive you can take that installation and distribute it out to other people by just giving them a copy of the directory. I haven't tested that part myself though...

I'm not familiar with msysgit, but can it use PuTTY's plink? If you don't know, plink is a simple command line ssh client, and it can use Pageant to authenticate.

Update: Yes, you should provide different documentation to your Windows users. (Unless you think that the Windows users are going to be using OpenSSH for something other than git access.) I think you're trying to force an equivalence that does not exist. It seems to me that you're trying to "[make] ssh easier" by making it harder.