Itinerary helper

Man, do I ever struggle picking flights. There are sooo many variables at hand that could save money or travel time or open up a new opportunity. Which airline should I fly? Should I just stick with the my local airport or surrounding alternatives? and the same question applies to the destination end (which requires a visit to google maps for a geography lesson). What time of day should I fly to save the most money yet be realistic considering parking, shuttles, and security delays. After about an our on expedia.com, my nerves feel like I am gambling at a craps table. Finally a solution that can dynamically shift airlines, departures, arrivals, airports. Kayak.com seems to be a tool I will highy value for preparing an itinerary. Check it out: http://www.kayak.com