I know having an ideal environment is damn near impossible, but how confident do you feel about your servers, AD, Exchange, etc?
I finally feel like I am getting where I want to be. All my servers are 2008 R2 and many are 2012 R2. All of our Computers and Servers are up to date (some need 2-3 updates). I have 2012 R2 Data Center licenses for all virtual hosts which gives me the ability to upgrade all of our severs to 2012 R2
All of our PCs in the entire organization are one model. I have all the images I need, and I run windows update on the images each month to keep them fresh. Break/Fix tickets are becoming less and less.