I was hesitant to switch completely to linux due to Visual Studio and MS Office. Those are 2 top notch applications. MS Office is a pain to install on Linux with WINE. I stopped doing Windows and .NET development, so I was just left with Office. I would strongly recommend getting Crossover office. It will install anything that requires Wine to run the application. [They also assist with Wine development] It will also grab the prereqs that the application requries.
Personally, I don't like Ubuntu that much. They try to push too many applications your way that you may not want. I've been a long time user of Gentoo Linux and recently Arch [which replaced my Ubuntu box].
Also another thing: Learn how to use SSH. Not just for casual shell access, really learn about the other features.
I found this resource to be very helpful on that: http://theexceptioncatcher.com/blog/2012/10/ssh-mastery-a-book-review/