Gerunds vs Infinitives – ‘Want Someone to Do Something’ vs ‘Want Someone Doing Something’

This is a rather authoritative way of stating categorically that you don't want something to happen generally or habitually, instead of just one time. The key is the progressive - which makes the prohibition somewhat habitual, as if thwarting the onset of a habit or tendency you want no part of.

For example, in the last example, the speaker could be talking to his son, who just got a car and has been home late a few times. Or a daughter that has started dating. Saying just "I don't want you to come home late" could be used for one occasion = tonight, after the prom, etc.

Having said that, the same father could say "I don't want you coming home late" in reference to one occasion, and it is merely a very authoritative restriction, and still carries a meaning of "tonight or any other night."

In (1) and (3) the speaker doesn't want these to become a regular thing; In (2) the speaker wants him to cease ALL inquiries - "stop asking around!" In (4) the speaker doesn't want the fact that the listener has a broomstick to become common knowledge.

"Learned riding" is grammatical but feels a little clunky. I suspect it's because we expect to see "learned [noun]" or "learned [to verb]" and, while "riding" can certainly be used as a noun, it's most commonly a verb when it's used on its own: you'd normally specify what you were riding if you were using it as a noun (e.g., "horse riding", "bike riding", etc.). In contrast "He learned programming" does sound natural because "programming" is commonly used on its own as a noun.

So I would say that "Ever since he was five, he learned riding" is OK but "Ever since he was five, he learned to ride" or "... he learned horse/bike/camel riding" would be better.

Even better still is "... he has learned", since the phrase "Ever since" implies an action that began in the past but is continuing into the present.