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Does repeating prepositions in a sentence sound more or sound less natural? For example in the following example, What sounds more natural?

This dog likes to yawl and hiccup.

or

This dog likes to yawl and to hiccup.

1

Like so many situations in English, how natural it sounds will depend on both context and intent.

As a general rule, we like to take shortcuts in English, so if the meaning remains unaffected, dropping (or "eliding") the second preposition in sentences like this is both common and natural. By extension, if there's no apparent reason to repeat it, the repetition may sound a bit unusual. However, there are several reasons why you might choose to repeat it due to context and/or intent:

  • emphasising that both words are important. A typical way to do this is in spoken English is to stress the word "and" (in written English, we would show this with bold or italic font: "This dog likes to yawl and to hiccup"), and in this situation it sounds natural to repeat the "to".

  • giving the statement a sense of formality, for instance as part of a speech. As shortcuts tend to be associated with informal or conversational English, not taking the shortcut conveys a sense of properness and formality.

  • wanting to sound very correct and exact, perhaps even pedantic, for example in a police report ("the accused began to swear and to spit"), in legislation ("to facilitate and to promote learning"), or in a grumpy old grammarian's classroom (well, that's the way a particular high-school English teacher of mine used to speak!).

The one other situation where it's natural to repeat the "to" is in a longer sentence where the bare infinitive (i.e. without "to") would be well separated from the to-infinitive, typically because of intervening objects, phrases or clauses. For example:

I've been authorised to provide information about the duties that you will carry out and to instruct you in the necessary procedures.

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Chappo's answer is correct, but I have another piece of advice.

When you include the to before each verb, it is clear that you are talking about two different actions: The dog likes to yawn and the dog likes to hiccup.

Without the second to it's possible to analyse that statement as describing one action with two parts: The dog likes to yawn-and-hiccup. It doesn't like a yawn or a hiccup on its own. Whenever it yawns, it must also hiccup. Whenever it hiccups it must also yawn.

That's a strange example, but consider these:
I like to walk along the beach and go fishing
I like to walk along the beach and to go fishing

In the first example, fishing is connected to walking along the beach. There's one action (with two parts) that the speaker likes: walking along the beach and then while walking along the beach, fishing (from the beach).

In the second example, there is not necessarily any connection between walking and fishing. The speaker likes walking and likes fishing but does not necessarily like walking and fishing at the same time.

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