With Server 2008/R2's end of support coming in January 2020, we've seen quite a few posts lately about replacing 2008/R2 servers (and even 2003 servers still).

People invariably point out that this should have been happening several years ago, but the reaction is most commonly 'We don't work in an ivory tower like you guys'. Huh? The 'ivory tower' guys were doing it like 7 years ago (when 2012 was released).

I do appreciate there's external costs and factors... But these are conversations and budgets that needed to be materializing... 3-5 years ago. We're in the planning phases now of getting rid of our stuff that still runs on 2012/R2. This could a couple years for a few systems, but we're not waiting until mid-2023 to start this process. I want to present budgetary numbers to my VPs for FY2020 for these remaining systems.

So... What does /r/sysadmin think? When did you get rid of most/all of your 2008 systems? Were there any substantial costs involved with any particular systems? If you're still dealing with important 2008 servers in production - what are the road blocks (and why is it taking so long to resolve)?