I use msysgit daily on Windows 7 against a github account. For the most part things work fine but there are a few things that annoy me:
- Disagreements about case insensitive paths sometimes confuse git. Renaming a folder simply to change its case is the most common one that catches me.
- I run everything through the bash shell which works fine but is a pain to connect to Windows batch files. This makes automation harder than required.
- Line endings... I just turn off any automatic conversion and use a decent editor that doesn't mind.
I initially used the GUI that comes with it and that works fine but I find the command line faster to work with. The advantages of git make the above problems worth it to work around for me.
I don't run my own server so can't comment on that. From what I have read linux setup would be much easier to do.