We had about 100 servers in 40 different sites that didn't support 2008 or above so we had to purchase a lot of new hardware.
We didn't dare to go to 2012 yet so we put 2008 on all of them. We barely finished those earlier this week.

Unfortunately, the ones that are killing us are the ones in our two main data centers. We were dumb enough to think those would be easy because hardware wouldn't be an issue. What we failed to recognize until January or February is that the stuff in our primary data centers is the stuff that's so much more difficult to move. I've been here for over a decade and I'm not sure about dependencies related to this stuff.

We even had 4 separate sharepoint 2003 farms with about 3 TBs of databases attached to them.
It's been a nightmare. I've known our CIO for about 15 years and he's always so calm. I think he cries himself to sleep most nights now. I feel bad for the guy. We should have done better for him.

We still have over 100 servers to go.

I think we're going to be saved though. Support for 100 servers for a month is available for 75k. We'll probably end up going down that path for a while.