I shall try to answer the questions, and then must go offline for a few days, as I am violently sick with God only knows what. The rule is not taboo to talk about. It is not even taboo to ask another Jew about his level of observance, although it is only rarely done. What IS taboo is to make value judgements ABOUT another Jew's level of observance. This is considered to be extremely rude, and will be quickly met with a "Go fuck yourself" response. Its like going into someone's house as their guest and criticising the decor.
It is, of course, perfectly legitimate to ask, if one is a guest in another Jew's home, what level of kosher they keep, so you know whether you are able to partake of the food. But, usually, asking isn't necessary. If you are an Orthodox Jew and you are in a Reform Jew's home, you can probably be pretty sure that he doesn't keep strict kosher to the degree that you do.
In terms of what are classified as clothes and what are not, I suppose that definition COULD have changed over the years. In fact, to be honest, it probably has. Could that have caused "issues"? Perhaps so. I just go with the most common interpretation, and leave it at that.
For me its not that I don't take the rule seriously. I fact I do. Its that I am trying to follow the other 612 (quite literally; there are 613 Commandments of the Law), and something has to give!
Seriously, it is hard for a Jew, almost impossible, to follow all the commandments (of which for men currently performable today in the absence of a Temple there are about 230, and for a female about 270 [the laws on female cleanliness provide a few more for her]). So, we do the best we can. We are not perfect. But every day we strive for greater observance, and to be better Jews.
I appreciate the questions, sincerely. But I have to ask for a pause for a few days, as I am very sick with some kind of bronchial infection that is just making me want to lie abed and get well. I shall come back when I feel better. Thanks.