1) He can't speak Chinese or Taiwanese even though he has lived in Taiwan for ten years.
2) He really needs to borrow some money from you. Would you lend him any?
For the first sentence, English usually uses "or" to separate between two things that a person cannot do. We also say "even though" instead of just "though" when the situation the person is in means we expect that they should be able to do what we're saying they cannot.
For the second sentence, I'm assuming the person who needs to borrow some money from you is also the person you're being asked to lend to. Therefore, you must make sure the gender pronoun matches (if it's a "he," then it needs to be "lend him" and not "lend her").