DoH over Tor already exists, but more importantly, Oblivious DoH (kind of like DoHoH) is being standardized by the IETF: https://datatracker.ietf.org/doc/draft-pauly-dprive-obliviou...
ODoH isn't going to be defeated by TLS MitM afaik.
This means that the DNS response for the web server would always be the proxy itself, or some set of proxies (and it would have to be the same IP for both wanted and unwanted traffic). What does DNS even add at that point? You'd be better off just making your "wanted" and "unwanted" servers the same server.
Few of these ideas can be expected to work unless Evil, LLC controls the program the end user chooses to read the web. When an advertsing services company is also the majority share "web browser" vendor, then ideas like this become feasible. Whereas if web users can choose any client to access the web,[FN1] then these ideas would be non-starters. The open source text-only browser I am using is not going to read the IP address of an ad server embedded in a web page and connect to it automatically. Even if it did, I would simply edit the source code to disable that behaviour and re-compile.
1. In theory they can but in practice they generally don't.
So you won’t necessarily even get to play this cat and mouse game - the dns requests are indistinguishable from your web requests.
I guess you could mitm your own ssl traffic and strip out dns answers there?
But then … how soon until we see DoHoH?