There is still plenty of Window Server using enterprises churning out .Net Framework code that must run on IIS. It's shrinking market for sure but it's still a market.
If they are willing to spend money on Windows Server, 3k a year to make it not less painful is probably worth it. Remember, any company using Windows Server is not hiring skilled DevOps/SRE/Ops, it's probably average at best, low paid workers. It's the type of people who have probably never heard of HackerNews either so it makes advertising here an interesting choice.
we still use windows server and IIS, and I can assure you we're never spending 3k to make anything less painful. our middle name is pain. and we bill hourly for that