Please ask unrelated questions in separate threads, with a title specific to each. You'll get quicker answers that way.
3. In this context, may and might are both acceptable, with no significant difference between them. (may or might would have been a good title for this question.)
A good title for #1 would be I've visited a teacher, doctor and an artist .., and for #2 — Don't/Won't you ever dare to venture ...
Student or Learner