I'd say "How many jobs have you had" if I was making a general question and I wasn't concerned whether you were working now or not. If I particularly wanted to know how many jobs you've had before the one you are working now, I would say "How many jobs have you had before". That's just my preference.
For your 2nd question, "Let's go say hello to him" is perfect. There's lots of variations of course. Myself I'd probably say "Let's go and say hi to him" I'd say the name of the person, though and not "him" if it was a mutual friend.