I can't be bothered to fill out the whole thing (partly because the categories are a bit vague, but mostly because I actually realize that I don't know the grammars of enough of the world's languages to give good answers for these questions instead of just regurgitating the standard linguistic Rogues Gallery: !Xoo, Dyirbal, Piraha, etc.), but I'll note that for #1 that I have seen Sumerian in the Greek alphabet, Sogdian in the Brahmi script, and Aramaic in Demotic, which are a bit wacky. There's also Old Nubian, an extinct Nilo-Saharan language written in the Coptic alphabet.
I really don't see what's so weird about the Turkish or Zulu alphabets. I suspect that it's because you're just glancing at individual letters and going "<c> for /dZ/! <q> for /k!/! How wacky!1!1!", without looking at how the orthography works as a whole-- Zulu, for instance, is actually a pretty elegant solution for romanizing an exotic phonology. My favorite example of what I'm talking about is Yup'ik: it uses <gg> for /x/ and <'> for /:/, for instance, which might make superficial people go "How wacky!1!1!", but the way the entire system works together with the language's phonotactics, it ends up being a very elegant and concise system. If you're looking for a romanization that really is ridiculous, look at Vietnamese, which writes /s/ with <x> for pretty much no reason.
As for the orthography question, I am confident other people are going to jump on Tibetan because of the famous <bsgrubs> = /d`up/, but again I must stress that the common opinion here is misguided: Tibetan's orthography is etymological and hopelessly out-of-date, but it is also almost entirely predictable and regular, unlike English. A better example I would suggest (though I have not studied the language, and it is possible that underneath the surface there is, as in Tibetan, an intelligible system) would be Burmese. This is an example sentence (from The World's Writing Systems), in transliteration and phonetic transcription:
pāḷiare:asā:saññ mranmācāare:asā:kui atōpaṅ lhwam:mui:khaịhantūsaññ.
palí-ʔəjèʔəθà-ði myãma-sa-ʔəjèʔəθà-go ətɔbĩ hlũ̀mmò-gɛ́-hãtu-ði
For "out of family" features, other than the obvious Dahalo, I'd like to nominate all the Iranian languages that have developed pharyngeal consonants. Why, Kurdish, why?