Yes relatively rational actors such as yourself are one thing but there is a lot of FUD out there around “will we be able to find anybody to work on it”, “will the vendor disappear one day”, etc. In my view these concerns are mostly specious (even MSFT could disappear one day, that is exactly why your have source code escrow agreements and the like; to me, any language environment has its mix of up and downsides and one can find enjoyment working within those constraints and there are ways to keep current / expose your team to an interesting mix of technologies). But the reality is that a lot of people making such decisions are political animals who advance to the level of their own incompetence by making “safe”, non-controversial decisions that don’t have to be defended to anyone and are fairly airtight. Also, they often read magazine articles and pick up the buzz about the latest & greatest and feel no one can fault them for staying with those supposedly ascendant technologies. So they go with magic silver bullets and by the time the decision proves a bad one they have been promoted somewhere else.
I was a little slow on the uptake so didn’t get a chance to investigate but there was a job on Dice a couple of weeks ago where supposedly someone was looking for deep FoxPro expertise here in the year of our Lord 2023. I could have probably been a shoo-in for that despite being rusty as hell (haven’t touched FP since about 2007, but I wrote books and authored and taught courseware on the product and was tech editor of FoxTalk for several years). Someone has clearly decided that something ain’t broke and shouldn’t be fixed – just maintained and extended. Depending on the company, the management and their reasoning process and strategy, I might have actually gone ahead with that retro-computing assignment. But I am sure they are finding it very hard to locate expertise or to hold onto developers in-house for a “dead” language that has to be coaxed to run on modern versions of Windows. That’s of course a somewhat different question from a still-living platform with questionable staying power, but it’s not entirely unrelated, either.