I did my travel plans and booking through Small World Vacations. They were awesome. I worked with a lady by the name of Daisy and she was great. Small World Vacations does not charge you a fee. They book directly with Disney and earn commission that way. They also look for any discounts that may come up before your final payment and will notify you of a better deal. I would HIGHLY recommend them to anyone.
As far as the time of year we went, I think we went during a pretty good time. The only place that was crowded was the Magic Kingdom. And like I told Kent, the Magic Kingdom is probably always crowded or at least more crowded than the other parks at any given time of the year. The weather was still hot but not unbearable. It was nice to be able to take a day off from the major parks and hit up one of Disney water parks which we wouldn't have been able to do if we went later in the year.
I did a lot of research on the internet and found two sites to be the most help. Those two sites being MouseSavers.com and Allears.net. They had tons of inside info on what to do, what not do to, packing lists, discounts, etc. I also was a daily visitor to Disney.com once I set up our reservations. They have a cute little countdown that lets you know how many days until your vacation and they will keep track of all your reservations to various shows and restaurants. Also, Disney will send you a free planning DVD that gives you a look at all the parks.
I also asked a lot of people who had gone for their advice. What worked for them, what didn't, what would they have done differently, etc. I got some of my best tips from friends who had gone before. Plus, it's easier to learn someone else lessons than having to learn the hard way on your own. :)
And lastly, if all else fails... Google.
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