First of all, not all things will dissolve in acid. In fact, plastics are typically very resistant to acids, and it depends heavily on the acid being used. Acid is not a magical solvent that dissolves everything it touches.
The answer to your main question though is that it’s not that bad, but potentially could be. The biggest issues are that repeatedly filling the bottle could peach out some chemicals used in fabrication of the plastic, thus weakening it, and putting those chemicals in the water you drink and also getting micro plastics into your drink. This is speculation at this point because serious studies have afaik not been done on the subject. To craft an analogy imagine making a cup of hard salt. Fill it up and let the water sit. It will dissolve some salt into saturated. But if you keep filling it up and enjoying it, you will dissolve more and more of the salt from the cup. That’s the basic concern.
Additionally normal wear and test weekends the plastic intended for a single use, it isn’t designed to what’s being repeatedly used. This will certainly cause issues with the structural integrity of the bottle leading to failure and probably micro plastics in your drink.
And finally the thing we know happens: UV radiation destroys plastic. The longer you use the bottle, the more time the sun has to work on degrading it. So the act of redoing it isn’t the problem it’s the fact that you’re using it more that matters. This would suggest that riding it a few times is probably fine. But don’t keep using it forever. Honestly you’re probably going to notice issue 2, the crushed bottle, before it’s harmful depending on the bottle type.
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