While it is prohibited by the ICANN policy [1], it is not strictly enforced so that there are multiple TLDs with A/AAAA records. They traditionally could be resolved with a trailing dot (thus it is not a dotless host name, that would have no dot), but nowadays many browsers refuse to resolve them without an explicit scheme. But they do still exist: try `http://pn./` for example.
At least for https://www.fi/ the case is that someone registered "www" as the domain name in the early days.
ai. 209.59.119.34
cm. 195.24.205.60
dk. 193.163.102.58
gg. 87.117.196.80
je. 87.117.196.80
pn. 80.68.93.100
tk. 217.119.57.22
uz. 91.212.89.8
ws. 64.70.19.33
But I agree that these domains are now out of luck, given that browsers no longer even remotely support them.Secondly, we have the expectation that subdomains of a given domain are run by the same entity, and represent natural semantic subdivisions. E.g. there's google.com, the over-arching website for all of Google and its first major product, and then for its other major products there's maps.google.com, mail.google.com, docs.google.com, etc.
This doesn't work with nyc, because subdomains of nyc are actually registrable domain names all their own that are controlled by other entities. So you can't have nyc be the overarching website for NYC, and then have parks.nyc, housing.nyc, business.nyc, etc., as natural subdivisions of it, because other people can own those domain names! So now you have no great way to subdivide up your site, and other people's sites are easily confusable as yours.
The only real way to do a dotless root DNS website is if you control the entire TLD; it has to be closed and not open to registration by external parties.