StraTaGeecal Thinking

So, I have been running over how we got totally rolled in the first Mid-Winters race a couple of weeks ago. There were more than a few mistakes I made, from sail trim to the start of the race. The next race will be along in two weeks and I am trying to think how I will do it differently. So here is a diagram and explanation of what happened at the start of the last race. Any thoughts on what might be a better strategy for the start assuming similar circumstances?

Here is the text from the right side of the diagram:
This is not to scale.

The start line is between two channel marks and the distance across the line is long, maybe 150 meter (took about two minutes to run the length of it in the wind conditions). Thus the green star was a good bit closer to the next mark than the orange square.

My thinking had been to pass just behind the black boats (who are on starboard here) in the red boat. This didn’t work out well for two reasons. I hadn’t counted on just how much the dirty air from the fleet would slow and affect my pointing.Thus, Red missed the green star, had to tack back (thus a terrible start).

So, next time I stick with the fleet, make the green star and roll over onto port tack? If I go too soon then I am the leeward boat and every faster boat (pretty much all the boats) pass red on the windward side giving more bad air or just stay on starboard as long as possible before tacking in an effort to “get above” others before heading off to the blue star?

Any thoughts? What am I missing?