The Federation has more advanced technology?
Let's take a look at history to see how much that matters:
VIETNAM: The US is more technologically advanced than the Viet Cong, yet the Viet Cong prevents any kind of strategic victory by the US on the battlefield and helps the north win a political victory anyway.
...And? The technological gap between the US and Vietnam is not nearly as large as the gap between the UFP and the Imperium.
AFGHANISTAN: The Soviet Union was more technologically advanced than the mujaheddin. They also spent the same amount time there trying to win. They also suffered a political defeat.
Uh-huh, noted.
AFGHANISTAN: The US is more technologically advanced than the Taliban. We went in in 2001. We're still there.
The Taliban aren't exactly fighting a straight up war, are they? They're made up of small celled groups that make raids on the US troops in the area (or wish to). This isn't the same as being a military power.
Tech don't beat determination and sneakiness.
Uh, yeah, yes it can. Because the technological advantage that Starfleet has over the Imperium is far greater than the US and the Taliban. It's far wider than 2012 US and any power during World War I.
Add in the fact that the Fed military is run by Greenpeace, and the Federation is, as I said, f***ed.
Yeah...no they aren't. They're much nicer and moral than any real military is, but they, as I've said, have some very sharp nasty teeth when they want to. In regards to being run...let's see just how that works with admirals, shall we?
Admiral Catwright: Conspired with elements of the Klingon Military to assassinate the current Chancellor to end peace talks and to provoke a war the Klingons couldn't win, even at the risk of the Enterprise and their crew.
Admiral Pressman: Was involved in an illegal Starfleet phase cloak R&D project that went tits up. After covering it up as a captain, he later went back as an admiral to try and retrieve the project. He had superiors that approved of said project.
Admiral Alynna Nechayev: Ordered Captain Picard to forcibly remove colonists for the sake of a peace treaty. In the same breath, rebuked him for not using a ~16 year old as a weapon of genocide against the Borg.
Admiral Ross: Personally assisted Section 31 in removing a Romulan political official to ensure that Starfleet's mole kept the Romulans in the war with the Dominion.
Federation Council: Approved of forcibly removing the Baki or whatever they were called in Insurrection for the sake of medical research--backed down only when the Enterprise revealed the plot to the public.
And that's just the admirals and that's just off the top of my head. And most of those have had serious support within the Federation. Others have even gone rogue, like the one admiral who tried to put the Federation under military dictatorship until the Dominion had been dealt with.
And if we're going to start punching holes in military procedures...well, the Imperium still thinks that they're fighting World War II. Starfleet is going to steamroll the Imperium on the ground.