Ubuntu is by far most friendly distro that I know of. As far as Ubuntu updates destroying things, I have not experienced that using stable updates only mode. IF you change it and want to play with bleeding edge updates and softwares, then you've pretty much asked for instability. Usually comes out of the box readily connected to the internet with Wired LAN, but I can't say the same for wireless as many times I had to find drivers and sometimes even cannot get wireless to work due to the wireless device being too new and undeveloped/under development for Linux.
Alternatively, if you are uncomfortable which many would be first migration, you could play with WUBI which is an Ubuntu that will install inside of NTFS as though it was a windows Software and can even be uninstall normally. It does run as a dual boot so you can get a good feel for Ubuntu running native with your hardware.
Softwares from windows as said by others aren't so great, but some do work. Office 2007, Photoshop I have installed via WINE and works quite well (Not perfect, but very well). As for programming editors, ubuntu comes with GEdit which is a good alternative to Notepad++.
I also think you will find that many Nix distro will come with an option for you to run their OS on live CD or USB to get comfy with it before committing. I just migrated to Ubuntu last year and have been happily using it for my web development without a single problem. Just don't update to Unity yet. Let it mature and see how well things go.