Some responses to your ideas:

1. I’ve been a fan of the green wave for some time and think Milwaukee would be great for it. If you set the wave for 11-13 mph, cars can go 22-26 mph and get all the same “wave” benefits without really making much difference to AQ. The big barrier though is interconnecting twenty-something signals (south of Logan Sq.) to make it all work. And it’s even a bigger headache when you consider some of the special timing plans already in effect at some of the triple intersections (e.g. Mil/Ash/Div or Mil/Chi/Ogd.) Hopefully some cheap wireless interconnects can come into play to make this happen.
2. Yes.
3. @Steven – The third animation lets waiting left-turners know on-coming traffic still has a green even though through traffic in turner’s direction has all red. This would be good for eastbound Chicago at Milwaukee.
4. Don’t get me started on on-street parking.
5. I think Tom S. had a hand in that plan if you’re ever in contact with him.