I mean Visual Studio automatically has a way of deploying directly to IIS for years now. Also as others have added, IIS isn't even used anymore with the rise of caddy and nginx.
The pricing itself seems really steep as well $3K a year?!? I don't exactly know who this is targeting.
It is for when you want to have accountability of deployments and at least what we had in Octopus deploy I could promote versions from test/acc to prod based on triggers or manual click of a button.
So you can have build pipelines separate from actual deploy pipelines and manage artefacts built by the build pipeline. It is required in some environments, but totally useless and waste of time in smaller environments.
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.
Not painful enough to justify additional tooling in any case.