I have a similar workflow but use gitosis to manage the repo on my VPS.

I use the msysgit bash with the windows path and plink as you suggest above but in addition I use pagent to manage the SSH key.

To access my repos this is the order I take,

• Open Pagent and access my key (you only enter the passphrase here once if you have one and even if you do it remembers it for the whole session).
• Then open Git bash and add/commit/push/pull/clone as normal.

One caveat I will note is that I had to convert the key I created with the Git bash using Putty Gen (available on the same link above) so that Pagent could use it.

For Git Bash

If you are running msysgit (I am assuming you are) and are looking to run Git Bash (I recommend it over TortoiseGit, but I lean to the CLI more than GUI now), you need to figure out what your home directory is for Git Bash by starting it then type pwd (On Windows 7, it will be something like C:\Users\phsr I think). While you're in Git Bash, you should mkdir .ssh.

After you have the home directory, and a .ssh folder under that, you want to open PuTTYgen and open the key (.ppk file) you have previously created. Once your key is open, you want to select Conversions -> Export OpenSSH key and save it to HOME\.ssh\id_rsa. After you have the key at that location, Git Bash will recognize the key and use it.

Note: Comments indicate that this doesn't work in all cases. You may need to copy the OpenSSH key to Program Files\Git\.ssh\id_rsa (or Program Files (x86)\Git\.ssh\id_rsa).

For TortoiseGit

When using TortoiseGit, you need to set the SSH key via pacey's directions. You need to do that for every repository you are using TortoiseGit with.