Fellow consultant here that has seen a lot of similar issues. I am currently tasked with rewriting a Delphi application that supports business in the hundreds of millions of dollars annually. It was written by a guy in his garage in Alabama. He sold the source code to the former parent company of my client. We now have a vm of the image of the guys laptop and the heavily customized Delphi environment required to build this application should a change be required. Apparently he built a bunch of delphi ide plugins to configure the environment, and should you try to build it with the latest Delphi IDE, you are SOL.

> Windows 95 in a VM

Puh-lease! I log into a VMS server every day to access an application that saw it's last update in 1995. Which wasn't even deployed until 2001. It will be replaced this year with a Win95 era application, complete with acres of giant grey buttons, served over a Citrix link from VMs running Server 2008. Bleeding edge, boys, bleeding edge.

Statistically a new software project - especially if done by a team with no common history of past successes - is risky.

So, if business values stability over risk, I understand very well if they select very very very very long term support option rather than to create the product from scratch.

> 1 year support is a joke. That's not even enough time for a company that builds software to migrate.

It's not enough to finish writing the requirements. One of our customers won't touch anything unless 15 years of support is guaranteed. And that's what they get.

Yes yes, there is a WinXP PC in our department with screen covered with a white paper with large font size text "This PC is under remote operation by Structure department, Do Not Shut it down."

Obviously there is a highly domain specific application for our Civil & Structural works last updated 10+ years ago. No one familiar/willing to upgrade it's internal licensing systems to work on newer Windows. So here we go. Whoever needs to work on it, take Remote Desktop. Simple.

For some of this stuff (Autocad, I'm looking at you...) it used to be the case that you could shell out a one-time $$$$ and get a license for v5.0 that would work for all eternity. The companies even gave you minor upgrades to support new OSes.

But since these guys have now switched to a subscription licensing model, they no longer do that, so there are scattered XP boxen around running ancient versions of various expensive software that just keeps working.

"Reasonable prices" is only fair compared to, for example, Oracle's gouging. It's not that MS has actually reasonable support pricing, just that ELA maintenance has become a cornerstone of most CIO's IT budget so there's no real incentive to do anything differently. I think the more important factor here is that MS sysadmins are a dime a dozen and the ramp from supporting an on-prem data center to "Azure Cloud" is a lot lower than learning something brand new.