I'm sure Ex will chime in but like I told one of the guys I am coaching yesterday when I go I only go once and I'm all in. Either it stays away or I am cooked and done for the day.
As for when to go? I never go first and will usually go when one of two conditions is met
1. There is a break of 3-4 guys up the road that I think are strong enough to stay away - you need to know who is racing and how strong they are as well as who they have in the field with them. One of my strongest assets while racing is my ability to bridge gaps as it is based on pure horsepower something I have a lot of.
2. There has been a break that has been away and is about to be caught. I fire with a hard counter attack and leave it all on the line.

It sounds like you are mentally committed to it so do it. In the race report thread I want to hear one of two things:
1. Was in a break and it stayed away
2. Was in a break and was caught with 100m to go, heart rate was Z5 for the last 30 miles and I collapsed from exhaustion 20 meters from the finish and DNF'd

You get my point.