Replacing 2003/2008 servers before 2019 is not 'Ivory Tower IT'

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)?