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@olaf_von_pokemon
I tend to buy Sennheiser earphones.
Last lot I bought were the CX300 II ones. I don't know if it's because I try and take care of them -to avoid the very issues you identify- but they tend to last a long time. In years as opposed to months.
The current model has a beefed up jack bit which will resist the problems.
They are comfortable and they suit me as they have asymetric earphone lead lenghts (prob not describing it well) which I like.
I think the sound is really good too!
Sennheiser CX 300 II Precision Noise Isolating: Amazon.co.uk: Electronics