Jake,
I hear what you are saying. But I think you have the percentages wrong. The way you explain it it sounds more like you are talking 98 percent sure you will make it and only 2 that you will not. And you are taking in considerations for speed wind angles other boats etc.
It really sounds like you only take the cross if you feel you have a really good chance(98%) on making or it you do not it will be without any real impact on the right of way boat.

The problem is how other sailors might interpret what you are saying.

Dave you are not only wrong buy way out in left field. The actions you are endorsing will get you or another boat in real trouble or someone really hurt.