How does Present Continuous [used in repetetive situations] sound to a native speaker?

Usually, I would expect to hear this kind of thing with specific reference to a future timetable or schedule, for a specific duration.

For example:

Q: What are you doing on an evening over the next fortnight?

A: I'm playing football at 5 o'clock every day, then I'm going for coffee, and after that I'll probably be listening to music.

If there were no time frame specified (if it were just an unprompted statement), there'd probably be a blank look and a response of:

What do you mean? When?

Notice also some simplification/changing of terms.

I've changed the coffee part to just "going for coffee", as in this context you'd refer more to the general activity, and saying "drinking a cup of" would sound too verbose.

"I am usually listening to music" doesn't make sense for the time frame context, as "usually" references what has happened in the past. This context is a future projection, so you would use "I will probably be". This is kind of the future version of "usually": If I usually do it, then I'll probably keep doing it.

Note: I've made a few assumptions here, and if you want to provide a specific context, I can add something a bit more tailored to my answer.

Update: Sports Star Interview Context

You wouldn't use the "I am" form in that context, because the time frame is not specified/infinite.

That answer would be appropriate if the question were, "As part of your training to become a champion, what are you doing over the next few weeks?"

With that being said, that sounds quite informal, so most likely in that context you would hear, "What will you be doing?" And the answer would follow, "I will be...", etc. I suppose there's a sense in which "What are you doing?" (present tense projected to the future) almost conveys "I'll be there/am there with you", which would seem intrusive.

A General Rule

I guess a rule of thumb would be this: Use the "I am" form when you are projecting yourself into the future, and sort of living it as you speak it, or anticipating it as if you were going to be doing it directly.

For example, if you were going to a concert next week, you might say, "I'm going to the XYZ concert," even though you're not actually on your way now (notice also that the time frame, or in this case the time of the event, is implied; if others weren't certain of this, they'd ask you, "Which one?"). It's as though you're sort of on your way anyway, due to anticipation, as though everything you're doing currently is recognised as leading toward that.