On points 2 and 3 (Coffee with a stranger/Talk to a random girl), Pick up Artists (PUA's) get a lot of flak for being douches or just trying to sleep with a bunch of women but one thing they push that will help anyone in life is things that most introverts types just do not do, like how to chat with random strangers, pushing the envelope in all types of interactions and not being attached to outcomes. This has helped me out immensely in my personal and professional life. I like the guys from
http://www.rsdnation.com/ as they give lots of free advice.