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As for speaking Taiwanese, you’ll find a lot more people who speak Taiwanese as their primary language in southern and rural Taiwan.

Having been born and lived in Taiwan for many years, I must say that Taiwanese in general is used in less formal environments. Many people tend to switch to Taiwanese when they are joking around or just chatting.

As for Taiwanese, I also found most of friends claimed not to speak it well, but they mostly lived in Taipei. The few who lived outside the city would speak it with their mostly DPP supporting families. A lot of Taiwanese-Americans also use it - I knew several who were in Taipei to learn Mandarin as they’d only spoken ban-lam-gu and English at home in the States. I knew maybe five foreigners at the NTNU Mandarin Centre who took Taiwanese classes - I learnt a few basic phrases but could never be bothered trying to learn the tone system - I find Mandarin hard enough

We had the same thing with Gaelic - native Gaelic speaking parents who consciously decided to only speak English to their children. These parents had, of course, been through an education system where Gaelic was belittled at every opportunity, where they were told it was the language of the peasants and the uneducated… Thankfully not everyone bought into this and the language hasn’t completely died out. That said, Gaelic is still in a very fragile state.