Hi Usskg5.. That's a good way of looking at it, which explains a lot- I'm going to address this one fully later on because there are SO many holes and mistakes and questions! Almost ever power in this screwed up, and the war could have went either way...
Martok, Leyton, that ambassador in the season 3 final, Bashir. So four times in 5 years.
Not too bad pull given that the Dominion didn't know everything the Feds were up to shows that whatever measures that had were able to keep their secrets secret and we did not hear much in the way of significant sabotage by Founders. In fact during the war Dominion intelligence seemed to be mostly from conventional means. I can only recall the Female Changelings decree that the Federation had countered the Breen weapon at the end of the war as a piece of intel that just came out of no where. I think Weyoun asks her if she is sure so he hadn't heard and he was a lot more tied into the running of the war then the Founder.
In the intelligence gathering area, in a comparison between the Dominion and the Federation, I have to give the award to the Federation.
The Federation was able to locate the White Production Facility, a sensor array hidden in a nebula, a gigantic battleship, plots to assassinate political leaders, secret shipyards... and starfleet took advantage of each one of them...
The Dominion didn't seem to make as many discoveries that gave them such a edge, though even with those federation victories, they were still beating the Federation...
Federation Mistake during the prewar times...
1. Dax's response to the jem hadar- lack of diplomatic response..
This one was a pretty hot topic, how Dax responded to the jem hadar's warning that if the Federation didn't wish to continue 'offending' the Dominion, they would stop coming through the wormhole...
Dax's respons, and basically the Fedration's response was that the Dominion was mistaken if they felt that their actions would stop them from exploring the Gamma quadrant.
It's strange because after giving such a response, and what happened as a result, the Federation took great efforts to try to contact the Founders themselves just to give a message of peace.
The problem was that the mission was covert and involved ironically-coming into the Gamma quadrant!
The arguement for Dax's statement?
Granted, the Dominion doesn't own the entire Gamma quadrant, and the Dominion doesn't equal the entire Gamma quadrant. They don't own the wormhole, and from what Starfleet had heard about the Dominion, they were bullies who did not respect the rights of other civilizations..
So her response was appropriate from this point of view. A possibility however was that Starfleet was yet to see how dangerous the Dominion was and how aggressive they were-once that response was given, the Federation had a problem on their hands whether they wanted one or not...